Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13674-16-3, Methyl 2-hydroxy-3-phenylpropanoate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C10H12O3, blongs to alcohols-buliding-blocks compound. Computed Properties of C10H12O3

General procedure: A solution of diisopropylazodicarboxylate (DIAD, 10 mmol) in anhydrous THF (20 mL) was added dropwise to an ice-bath cooled mixture of ethyl or methyl phenyllactate (10 mmol), the suitable phenol (10 mmol) and PPh3 (10 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred overnight, under N2 atmosphere, at room temperature. The organic solvent was evaporated in vacuo, and a mixture of Et2O and n-hexane (40 mL, 1:1) was added to the residue. The resulting precipitate was filtered off, and the filtrate was evaporated to dryness. The residue was chromatographed on a silica gel column using the suitable eluent affording the desired compounds in 33-79% yields.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13674-16-3, Methyl 2-hydroxy-3-phenylpropanoate, and friends who are interested can also refer to it.

Reference:
Article; Piemontese, Luca; Fracchiolla, Giuseppe; Carrieri, Antonio; Parente, Mariagiovanna; Laghezza, Antonio; Carbonara, Giuseppe; Sblano, Sabina; Tauro, Marilena; Gilardi, Federica; Tortorella, Paolo; Lavecchia, Antonio; Crestani, Maurizio; Desvergne, Beatrice; Loiodice, Fulvio; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 583 – 594;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.124-76-5, name is Isoborneol, molecular formula is C10H18O, molecular weight is 154.2493, as common compound, the synthetic route is as follows.Computed Properties of C10H18O

In this case, the reaction of preparing camphor by dehydrogenation of liquid isoborneol is carried out in a membrane reactor. In this case, the isoborneol is an industry grade raw material. Since at room temperature, the isoborneol is a solid powder, it is first dissolved in xylene to form 30% solution. The mass reaction space velocity of the solution is 0.5 h-1. After it goes through a heat exchanger to achieve preheating temperature of 220C, it goes into the membrane reactor for dehydrogenation. The pipeline is filled with the GC250 Cu-Zn-Al catalyst produced by Japan NGC Corporation and the thermocouple casing was used to measure the bed temperature of any one of the dehydrogenation reaction tubes. After the oxygen passes through the flow meter, it goes through the center tube dedicated to oxygen gas in the tube. Oxygen permeates through the membrane to the shell and reacts with hydrogen. The molar ratio of oxygen to isoborneol is 1: 6. The shell is filled with Pt / Al2O3 oxidation catalyst prepared by multiple coating-impregnation method, wherein the load mass fraction of Pt is about 1%; the pressure on the dehydrogenation side is 0.6MPa, the reaction temperature is 220C. The film used in the reactor is a silicon dioxide film system manufactured by Sulzer Chemtech (SMS). Each tube has an inner diameter of 8 mm and an outside diameter of 14 mm. The product of camphor and solvent xylene in the dehydrogenation side enters the solvent recovery section for solvent recovery and recycling, and the camphor product is sent to the finished product area.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124-76-5, Isoborneol, and friends who are interested can also refer to it.

Reference:
Patent; Fuzhou University; Zheng, Huidong; Kong, Wei; Zhang, Jianwen; Lin, Yi; Yan, Zuoyi; Wang, Yingshu; Wu, Dan; (11 pag.)CN106365936; (2017); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 28539-02-8, 1-(Hydroxymethyl)benzotriazole, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 28539-02-8, blongs to alcohols-buliding-blocks compound. Product Details of 28539-02-8

(A) N-((1H-Benzo[d][1,2,3]triazol-1-yl)methyl)-N-benzyl-1-phenylmethanamine To a mixture of 1H-benzotriazole-1-methanol (10.06 g) and ethanol (250 mL), dibenzylamine (12.97 mL) was added at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the precipitate was washed with IPE to obtain the title compound (19.99 g). 1H NMR (300 MHz, DMSO-d6) delta 3.70 (4H, s), 5.58 (2H, s), 7.18-7.46 (11H, m), 7.54 (1H, t, J=7.6 Hz), 7.70 (1H, d, J=8.5 Hz), 8.08 (1H, d, J=8.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,28539-02-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; HIRAYAMA, Takaharu; FUJIMOTO, Jun; CARY, Douglas Robert; OKANIWA, Masanori; HIRATA, Yasuhiro; (147 pag.)US2017/44132; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 111-90-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 111-90-0, name is Diethylene Glycol Monoethyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of pure NaH (2.40 g, 100 mmol) in anhyd DME (100 mL) was slowly added 2-(2-ethoxyethoxy)ethanol (13.42 g, 100 mmol) at r.t. After stirring for 30 min, the now clear solution was treated with 3-bromoprop-1-yne (11.9 g, 100 mmol) in PhMe (2 mL) over a period of 15 min (violent reaction) with vigorous stirring. The resulting blend was heated to reflux for 4 h, allowed to cool to r.t., and filtered. Addition of H2O (300 mL) was followed by extraction with CH2Cl2 (3 × 100 mL), and the organic layers were combined, washed with H2O (3 × 100 mL), and dried (MgSO4). Evaporation of the solvents under reduced pressure and vacuum distillation of the residual liquid gave 6a as a colorless liquid; yield: 12.9 g (75%); bp 47-48 C/0.1 Torr. Employment of prop-2-yn-1-yl 4-methylbenzenesulfonate in DME instead of 3-bromoprop-1-yne generated 6a in only 40% yield. IR (film): 3251, 2975, 2868, 2114, 1444, 1349, 1289, 1246, 1107, 1033, 948, 920, 844, 671 cm-1. 1H NMR (300 MHz, CDCl3): delta = 4.19 (d, J = 2.4 Hz, 2 H), 3.68 (AA’BB’m, 4 H), 3.64 (AA’m, 2 H), 3.58 (BB’m, 2 H), 3.51 (q, J = 7.0 Hz, 2 H), 2.40 (t, J = 2.4 Hz, 1 H), 1.19 (t, J = 7.0 Hz, 3 H). 13C NMR (100 MHz, CDCl3): delta = 79.3 (CH), 74.3 (Cquat), 70.4 (CH2), 70.1 (CH2), 69.5 (CH2), 68.8 (CH2), 66.3 (CH2), 58.0 (CH2), 14.8 (CH3). MS (EI, 70 eV): m/z (%) = 173 ([MH+], 55), 127 (10), 117 (10), 103 (20), 83 (40), 73 (100), 59 (70). HRMS (EI, 70 eV): m/z [MH+] calcd for C9H17O3: 173.1178; found: 173.1173.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 111-90-0, Diethylene Glycol Monoethyl Ether.

Reference:
Article; Dahlmann, Uwe; Vollhardt, K. Peter C.; Synthesis; vol. 52; 8; (2020); p. 1287 – 1300;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 62058-03-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 62058-03-1, name is trans-4-Aminoadamantan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of ethyl 1-phenyl-5-(2-methyl-4-oxobutan-2-yl)-1H-pyrazole-4-carboxylate 14b (45 mg, 0.15 mmol) in CHCl3 (9 mL) was added trans-5-hydroxy-2-adamantylamine (25 mg, 0.15 mmol), acetic acid (0.025 mL, 0.45 mmol) and sodium triacetoxyborohydride (85 mg, 0.45 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in methanol (0.30 mL), and added 1.0 N NaOH (0.22 mL, 0.22 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the solvent was removed under vacuum. The mixture of the residue in CHCl3 (1.5 mL) and DIPEA (0.078 mL, 0.45 mmol) and HBTU (35 mg, 0.15 mmol) was stirred at room temperature. After 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl., then purified with column chromatography (silica gel, eluting with CHCl3/methanol) to give the title compound as a white solid (0.025 g, 42 percent yield).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 62058-03-1, trans-4-Aminoadamantan-1-ol.

Reference:
Article; Udagawa, Shuji; Sakami, Satoshi; Takemura, Takahiro; Sato, Mikiya; Arai, Takahiro; Nitta, Aiko; Aoki, Takumi; Kawai, Koji; Iwamura, Tomokatsu; Okazaki, Seiji; Takahashi, Takehiro; Kaino, Mie; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1617 – 1621;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 440-60-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 440-60-8, name is (Perfluorophenyl)methanol, molecular formula is C7H3F5O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(a) 2,2-Dimethyl-3-dichlorovinyl-cyclopropanecarboxylic acid pentafluorobenzyl ester STR28 0.1 mole of 2,2-dimethyl-3-dichlorovinyl-cyclopropanecarboxylic acid chloride (cis/trans) was added dropwise at 70 C. to 0.1 mole of pentafluorobenzyl alcohol. The mixture was then heated at 120 C. for a few minutes until gas evolution ceased. The yield of an oil, which was pure by thin-layer chromatography, was quantitative. b.p.0.1 120-130 C. Spectroscopic data: IR (cm-1): 2,900, 1,740, 1,660, 1,510, 1,460, 1,415, 1,385, 1,355, 1,310, 1,220, 1,161, 1,130, 1,080, 1,050, 995, 970, 940, 810, 780. mass spectrum (m/e): 181, 163, 165, 91, 127, 109, 191, 207, 353, 388 (M). NMR (ppm): 6.6 and 5.6 d (1), 5.2 s (2), 0.8-2.4 m (8).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 440-60-8, (Perfluorophenyl)methanol.

Reference:
Patent; Bayer Aktiengesellschaft; US4183950; (1980); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 61487-25-0, name is (2-Amino-3-chlorophenyl)methanol, the common compound, a new synthetic route is introduced below. Quality Control of (2-Amino-3-chlorophenyl)methanol

Example 83 – Preparation of 2-acetoxymethyl-6-chloro aniline This material was prepared from 2-amino-3-chlorobenzyl alcohol and acetyl chloride by the general procedure outlined in Example 82. The product was isolated as an amber oil and was characterized by IR and 1H NMR spectroscopy and combustion analysis.

The synthetic route of 61487-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 5020-41-7, Adding some certain compound to certain chemical reactions, such as: 5020-41-7, name is 2-(3-Methoxyphenyl)ethanol,molecular formula is C9H12O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5020-41-7.

Step 2: Synthesis of l-(2-bromoethyl)-3-methoxybenzene: [0982] To a stirred solution of 2-(3-methoxyphenyl)ethan-l-ol (0.6 g, 3.94 mmol) in DCM, PPh3 (1.6 g, 5.92 mmol) was added and the solution was stirred at rt for 10 min. Then CBr4 (2.6 g, 7.88 mmol) was added at 0 C. The resulting reaction mixture was stirred at rt for 2 h. The progress of the reaction was monitored by TLC. Upon completion the reaction mass was diluted with water and extracted with DCM. The combined organic layers were dried over Na2S04 and concentrated under reduced pressure. The crude compound was purified by column chromatography to afford the title compound (0.725 g, 85%).

According to the analysis of related databases, 5020-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; WO2015/10049; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 52273-77-5, name is 2-(3-Aminophenyl)ethanol. A new synthetic method of this compound is introduced below., SDS of cas: 52273-77-5

Step 4 Preparation of 3-{2-[6-(4-fluoro-phenyl)-pyridin-2-ylmethoxy]-ethyl}-phenyl amine Using a similar procedure to step 1 of Example 1 222 mg (1 mmol) of the product of step 3 above was reacted with 137 mg (1 mmol) of 3-(2-hydroxy ethyl) phenyl amine. After purification on silica with 40% ethyl acetate:hexane elution, recovered 0.21 g (65%) of an oil. NMR (200 MHz,CDCl3) delta8.11 (m, 2H, ArH), 7.79 (m, 2H, ArH), 7.18-7.38 (m, 6H,ArH), 7.08 (d,J=8 hz,1H,ArH),4.63 (s, 2H, OCH2),4.53(bs,2H,NH2), 3.78 (t, J=7 Hz, 2H, OCH2), 2.92 (t, J=7 Hz,2H,ArCH2)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 52273-77-5, 2-(3-Aminophenyl)ethanol.

Reference:
Patent; Wyeth; US2003/203941; (2003); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.100058-61-5, name is 3-(Benzyloxy)cyclobutanol, molecular formula is C11H14O2, molecular weight is 178.23, as common compound, the synthetic route is as follows.Safety of 3-(Benzyloxy)cyclobutanol

Example lbb – Preparation of R Synthesis of 2-bromo-l-(bromomethyl)-l-(phenylmethoxy)ethane [0299] The mixture of 1 (60.1 g, 0.47 mol), benzyl bromide (80 g, 0.47 mol) and Hg2Cl2 (100 mg, 0.2 mmol) was heated to 150 C over night. TLC showed the reaction was completed. The product 2 (98 g, 70% yield) was obtained by distillation (180 C) in vacuum as a colorless oil. [0300] 1H NMR (400 MHz, CDCl3):7.37-7.28 (m, 5H), 4.65 (s, 2H), 3.82-3.77 (m, 1H), 3.56 (d, 4H, J=5.2 Hz). Synthesis of l-(methylsulfinyl)-l-methylthio-3-(phenylmethoxy)cyclobutane [0301] To the mixture of 3 (45.1 g, 0.36 mol) in THF (400 mL) was added n- BuLi (145 mL, 0.36 mol, 2.5 M) at -10 C under N2 drop wise. It was stirred further 2 h at this temperature. And then it was cooled to -78 C and the mixture of 2 (46.2 g, 0.15 mol) in THF (100 mL) was added drop wise over 0.5 h. The result mixture was stirred further 2 h at – 78 C and over night at r.t. It was quenched by the addition of H20 (100 mL) and the mixture was extracted with EtOAc (300 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluan: EtO Ac/Pet. ether= 1/2, v/v) to give the product 4 (30 g, 73% yield) as a yellow oil. [0302] 1H NMR (400 MHz, CDCl3):7.36-7.26 (m, 5H), 4.47 (d, 2H), 4.38-4.31 (m, 0.6H), 4.21-4.18 (m, 0.4H), 3.10-2.98 (m, 0.8H), 2.78-2.64 (m, 1.2 H), 2.55 (s, 1.2 H), 2.44 (s, 1.8 H), 2.42-2.15 (m, 2H), 2.12 (d, 3H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-one [0303] To a solution of compound 4 (30 g, 0.1 1 mol) in dry ether (500 mL) was HC104 (22.5 mL, 35%) at 0 C drop wise, while keep the temperature bellow 10 C . It was stirred further 2 h at 0 C and over night at r.t. Solid NaHC03 and MgSC>4 were added and the resulting mixture was stirred further 0.5 h at r.t. It was filtered and the cake was washed with ether. The filtrate was concentrate in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 5 (14.0 g, 72% yield) as a yellow oil. [0304] 1H NMR (400 MHz, CDC13): 7.39-7.25 (m, 5H), 4.52 (s, 2H), 4.40-4.34 (m, 1H), 3.26-3.10 (m, 4H). Synthesis of 3-(phenylmethoxy)cyclobutan-l-ol [0305] To the mixture of 5 (14.0 g, 79.46 mmol) in EtOH (150 mL) was added aBH4 (3.32 g, 87.40 mmol) at 0 C over 0.5 h. The resulting mixture was stirred further 2 h at 0 C and TLC showed the reaction was completed. The solvent was removed in vacuo and the residue was diluted with MeOH (100 mL) and quenched by HC1 (1M). The organic solvent was removed in vacuo and the residue was extracted with EtOAc (200 mL*3). The combined extracts were dried over Na2SC>4 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/4, v/v) to give the product 6 (14 g, 99% yield) as a yellow oil. [0306] 1H NMR (400 MHz, CDC13): 7.39-7.27 (m, 5H), 4.43 (s, 2H) 1H), 3.68-3.59 (m, 1H), 2.76-2.67 (m, 2H), 2.37 (br, 1H), 2.05-1.89 (m, 2H). Synthesis of 5-(phenylmethoxy)-2-[3-(phenylmethoxy)cyclobutoxy]pyrimidine [0307] To the mixture of 6 (10.5 g, 58.93 mmol) in DMSO (100 mL) was added NaH (3.06 g, 60%, 76.61 mmol) at r.t. The resulting mixture was stirred for 0.5 h at r.t, and then the mixture of 7 (13.0 g, 58.93 mmol) in DMSO (50 mL) was added drop wise over 10 min. The whole mixture was stirred further 0.5 h, TLC showed the reaction was completed. It was quenched by the addition of H20 (200 mL) and the mixture was extracted with EtOAc (200 mL*3). The combined extracts were dried over a2S04 and concentrated in vacuo to give the crude product. It was purified by column chromatography (Eluant: EtOAc/Pet.ether=l/5, v/v) to give the product 8 (10.0 g, 47% yield) as a white solid. [0308] 1H NMR (400 MHz, CDC13): 8.19 (s, 2H), 7.38-7.25 (m, 10H), 5.05 (s, 2H), 4.76-4.68 (m, 1H), 4.43 (s, 2H), 3.82-3.75 (m, 1H), 2.87-2.81 (m, 2H), 2.24-2.17 (m, Synthesis of 2-(3-hydroxycyclobutoxy)pyrimidin-5-ol [0309] To the mixture of 8 (8.84 g, 24.42 mmol) in dry DCM (250 mL) was added BC13 (100 mL, 1M in DCM, 0.1 mol) at -20 C under N2. The resulting mixture was stirred further 0.5 h at -20 C . TLC showed the reaction was completed, and then it was quenched by the addition of MeOH (20 mL). The solvent was removed in vacuo to give the crude product. It was diluted with DCM (50 ml) and the solid was filtered out by filtration. The cake was suspended in H20 (20 mL) and filtered, dried in vacuo to give the product (2.2 g, 50% yield) as a white solid. [0310] 1H NMR (400 MHz, DMSO-d6): 9.76 (s, 1H), 8.12 (s, 2H), 5.07 (br, 1H), 4.59-4.52 (m, 1H), 3.85-3.78 (m, 1H), 2.76-2.72 (m, 2H), 1.91-1.85 (m, 2H). LCMS [mobile phase: from 50% water (0.1% TFA) and 50% CH3CN to 5% water (0.1% TFA) and 95% CH3CN in 6.0 min, finally under these conditions for 0.5 min.] purity is >95%, Rt = 1.84 min; MS Calcd.: 182.2; MS Found: 183.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100058-61-5, 3-(Benzyloxy)cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; TRIUS THERAPEUTICS INC.; LAWRENCE LIVERMORE NATIONAL SECURITY, LLC; BENSEN, Daniel; BORCHARDT, Allen; CHEN, Zhiyong; FINN, John, M.; LAM, Thanh, To; LEE, Suk, Joong; LI, Xiaoming; TARI, Leslie, William; TENG, Min; TRZOSS, Michael; ZHANG, Junhu; JUNG, Michael, E.; LIGHTSTONE, Felice, C.; WONG, Sergio, E.; NGUYEN, Toan, B.; WO2014/43272; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts