Category: alcohols-buliding-blocks

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 4704-94-3, name is 2-(Hydroxymethyl)propane-1,3-diol. This compound has unique chemical properties. The synthetic route is as follows. 4704-94-3

Step a. 3-Methoxy-2-methoxymethyl-propane-1-ol Sodium hydride (60% dispersion in oil) (2.93 g, 73.2 mmol) was added to an ice-cooled solution of 2-hydroxymethyl-propane-1,3-diol (M. R. Harnden et al. J. Med. Chem. 1990, 33, 187) (3.53 g, 33.3 mmol) in DMF (100 ml) and the mixture was stirred at room temperature for 40 min. The reaction mixture was cooled with ice and iodomethane (4.56 ml, 73.2 mmol) was added, the stirring was continued allowing the mixture to reach room temperature over 24 h. The mixture was poured into ethyl acetate (300 ml) and washed with brine (150 ml). The organic phase was dried (MgSO4), and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, ethyl acetate) to afford colourless oil. 1H NMR (300 MHz, CDCl3) 3.72 (2H, d), 3.47 (2H, d), 3.45 (2H, d), 3.32 (6H, s), 2.07(1H, m).

Statistics shows that 4704-94-3 is playing an increasingly important role. we look forward to future research findings about 2-(Hydroxymethyl)propane-1,3-diol.

Reference:
Patent; James Black Foundation Limited; US6479531; (2002); B1;,
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7397-62-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7397-62-8, name is Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

a1 n-Butyl (t-butyl-dimethyl-silanyloxy)-acetate n-Butyl glycolate (231 g; 1.75 mol) and imidazole (345.1 g; 5.07 mol) were combined at 0 C. The suspension obtained was treated portionwise with t-butyldimethylchlorosilane (303 g; 2.01 mol) over 1.5 hours. After 20 hours at room temperature the reaction mixture was diluted with ether/n-hexane 1:1 (1 l) and suction filtered. The crystals were rinsed thoroughly with ether/n-hexane 1:1 (200 ml). The filtrate was washed in succession with water (2*700 ml) and saturated aqueous sodium chloride solution (500 ml), dried over magnesium sulphate and concentrated. The oil obtained was distilled over a Vigreux column (7.5 cm). Yield: 405 g (94%) as a colorless oil (b.p. 78 C./0.98 mm Hg). IR (film): 1760, 1225, 1206, 1148, 838, 780 cm-1; MS (EI): (M+H)+247.

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Reference:
Patent; Hoffmann-la Roche Inc.; US6218379; (2001); B1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 55414-72-7, name is (2-Amino-5-methoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. 55414-72-7

Potassium tert-butoxide (49.3 mg, 0.439 mmol) was dissolved in technical-grade THF(1.7 mL, containing ~0.2% H2O), and the solution was stirred at room temperature in air for 1 min.A solution of amide 6 (51.2 mg, 0.245 mmol) and 2-amino-5-methoxybenzyl alcohol (43.3 mg,0.283 mmol) in THF (0.8 mL) was added, and the mixture was stirred at room temperature in air for3 h. Water (20 mL) was added, and the mixture was extracted with ethyl acetate (20 mL). Theorganic layer was washed with 1M aqueous HCl solution (3 ¡Á 20 mL). The organic layer was driedover MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flashchromatography using 1:2 ethyl acetate / dichloromethane as eluent to give the title compound as awhite solid (13 mg, 17%).

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Reference:
Article; Wangsahardja, Jonatan; Marcolin, Gabriella M.; Lizarme, Yuvixza; Morris, Jonathan C.; Hunter, Luke; Synlett; vol. 27; 8; (2016); p. 1237 – 1240;,
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2919-23-5, 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 2919-23-5, name is Cyclobutanol. This compound has unique chemical properties. The synthetic route is as follows.

1-Bromo-4-cyano-3-fluoro-5-(4-ethyl-phenyl)-benzene (1.2 g) is added to a flask charged with a stir bar, KOfBu (0.5 g) and cyclobutanol (3.0 g). The solution is stirred at room temperature overnight, before another portion of KOfBu (0.2 g) is added. The solution is stirred for another 5 h and then neutralized with 1 M aqueous HCI solution. The resulting mixture is extracted with ethyl acetate, the combined organic phases are dried (sodium sulphate) and the solvent is removed to give the title compound.Yield: 1.28 g (92% of theory)

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 2919-23-5, Cyclobutanol.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/55870; (2008); A1;,
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927-74-2, 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 927-74-2, name is 3-Butyn-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of but-3-ynol (3.0 mL, 40 mmol) in dry CH2Cl2 (20 mL) was added N-methylimidazole (9.52 mL, 120 mmol), iodine (0.8 g, 120 mmol) and tert-butyldimethylsilyl chloride (6.63 g, 44 mmol). After 4-5 h at room temperature, the solution was washed with saturated aq. Na2S2O3, brine, and water, dried over MgSO4 and evaporated under reduced pressure. Purification of the residue by column chromatography (hexane:EtOAc, 9:1, Rf 0.9) gave protected butynol 7 (7.1 g, 90%) as an oil. deltaH (400 MHz; CDCl3) 0.06 (6H, s, Me2Si), 0.89 (9H, s, tBu), 1.94 (1H, t, J 2.4, CH?C), 2.39 (2H, dt, J 2.4 and 7.2, OCH2CH2), 3.73 (2H, t, J 7.2, OCH2); deltaC (100 MHz, CDCl3) -5.31 Me2Si), 18.3 (CMe3), 22.8 (OCH2CH2), 25.8 (CMe3), 61.7 (OCH2), 69.2 (CH?C), 81.5 (CH?C); IR, numax/cm-1 2857 (C-H), 2122 (C?C), 1472 (C-H), 1103 (C-O).

Statistics shows that 927-74-2 is playing an increasingly important role. we look forward to future research findings about 3-Butyn-1-ol.

Reference:
Article; Iqbal, Amjid; Sahraoui, El-Habib; Leeper, Finian J.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2580 – 2585;,
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42514-50-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 42514-50-1, name is 3-Amino-3-methylbutan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

a. Tert-butyl (3-hvdroxy-1 ,1-dimethylpropyl)-carbamidate200 g (1.94 mol) 3-amino-3-methylbutan-1 -ol in 0.75 I ethyl acetate are combined with a solution of 435.0 g (1.99 mol) di-tert-butyl-dicarbonate in 0.75 I ethyl acetate within one hour. The reaction mixture is stirred for 30 min and the solvent is eliminated in vacuo. The residue obtained is used in the next step without further purification. Yield: 412.5 g1H-NMR (DMSO, 400 MHz): 1.19 (s, 9H); 1.36 (s, 6H); 1.68-1.74 (m, 2H); 3.42-3.50 (m, 2H); 4.39 (t, J = 4.8, 1 H); 6.36 (br s, 1 H).Alternatively, tert-butyl (3-hydroxy-1 ,1-dimethylpropyl)-carbamidate may also be prepared by the methods described for example in J. of Labell. Compounds & Radioph. 2001 , 44(4), 265-275 or WO 03/037327, p. 82/83.

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Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/132162; (2008); A1;,
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27489-62-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 27489-62-9, name is trans-4-Aminocyclohexanol. This compound has unique chemical properties. The synthetic route is as follows.

(To a reaction flask, DMF (2 L) was added, 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-(3-chloro-4-methoxybenzylamino)pyrimidine-5-carboxylic acid (300 g, 0.8 mol) was added under stirring, DIEA (209 mL, 1.2 mol) was added dropwise under ice-water, then HATU (456 g, 1.2 mol) was added, the mixture was stirred for 30 min, trans-4-aminocyclohexanol (138.2 g, 1.2 mol) was added. The temperature of the reaction was naturally elevated to room temperature, stirring was carried out for 2 h, and TLC was used to monitor the reaction. After the end of reaction, the reaction liquid was poured into water (3 L) to precipitate solid and filtrated, the filter cake was washed with water, air-dried, then recrystallized with acetone twice to obtain white solid (240 g, yield of 63%).

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, 27489-62-9, trans-4-Aminocyclohexanol.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Shu, Chutian; Wu, Yongqian; (34 pag.)US2016/46654; (2016); A1;,
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1805-32-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1805-32-9 as follows.

General procedure: Cu/OMS-2 (10 mg, 0.25 mol%), benzyl alcohol (2 mmol), N-arylamidine (0.5 mmol), toluene (2 mL) were added to a flask with a bar. The flask was stirred at 90 C for 20 h under air. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered. The filtrate was removed under reduced pressure to get the crude product, which was further purified by silica gel chromatography (petroleum/ethyl acetate = 40/1-50/1 as eluent) to yield corresponding product. The identity and purity of the products were confirmedby 1H, 13C NMR spectroscopic and HRMS analysis.

The chemical industry reduces the impact on the environment during synthesis 1805-32-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Meng, Xu; Bi, Xiuru; Wang, Yanmin; Chen, Gexin; Chen, Baohua; Jing, Zhenqiang; Zhao, Peiqing; Catalysis Communications; vol. 89; (2017); p. 34 – 39;,
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Adding a certain compound to certain chemical reactions, such as: 23377-40-4, 3-(Hexadecyloxy)propan-1-ol, 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, 23377-40-4, blongs to alcohols-buliding-blocks compound. 23377-40-4

3-(Hexadecyloxy)propan-1-ol was synthesized in one step according to the method ofYamano, Y. et al., Biorg. Med. Chem. (2012) 20:3658-3665 and recrystallized from hexane. The crystalline product (200mg, 0.67mmol) was dissolved in dry CH2C12 and diisopropylethylamine (0.70 mL, 2.68 mmol, 4 equiv) was added while stirring at RT. 2- Cyanoethyloxy(N,N-diisopropylamino) phosphonamidic chloride (0. l8mL, 0.8mmol, 1.2 eq) was added dropwise and the solution was stirred for 45mm. After completion lSmL of CH2C12 were added and the organic phase was washed with saturated aqueous NaHCO3 anddried over MgSO4. The crude product was purified on a silica column with Hex:EtOAc:NEt350:50:1 as eluent to afford the title compound as a colorless liquid (175mg, 52% yield). Rf inEtOAc =0.28. MS (ESI): found 501 (M+H); mass expected for (C28H57N203P + H = 501.4).?H NMR (400 MHz, CDC13) 0.89 (t, J=6.85 Hz, 3H, CH3CH2) 1.19 (dd, J=6.72, 3.42 Hz,12H, 2 (CH3)2CHN) 1.26 (s, 26 H, 13 (Cl2)11) 1.56 (quin, J=6.94 Hz, 2H, OCH2CH2CH2)1.88 (quin, J=6.30 Hz, 2H, POCH2CH2CH2O) 2.64 (t, J6.60 Hz, 2H, CH2CN) 3.40 (t,J=6.66 Hz, 2H, OC1j2CH2CH2) 3.50 (t, J=6.30 Hz, 2H, POCH2CH2CLLaO) 3.54 – 3.65 (m,2H, 2 CH) 3.65 – 3.79 (m, 2H, POC1j2CH2CH2O) 3.79 – 3.93 ppm (m, 2H, POCH2CH2CN).?3C NMR (101 MHz, CDC13) oe 14.1 (s, 1C, CH3CH2) 20.3 (d, J6.60 Hz, 1C, CH2CN) 22.7(s, 1C, CH2CH2CH3) 24.5 and 24.63 (2 d, J=7.70 Hz, 2x2C, (CH3)2CHN) 26.2 (s, 1C,OCH2CH2CH2) 29.3 (s, 1CH211) 29.5 (s, 1CH211) 29.6 (s, 2CH211) 29.6 (s, 1CH211) 29.7 (s,5CH211) 29.8 (s, 1CH211) 31.5 (d,J7.34 Hz, 1C, POCH2CH2CH2O) 31.9 (s, 1CH211) 43.0 (d,J=1 1.74 Hz, 2C, 2 CH) 58.3 (d, J=19.07 Hz, 1C, POCH2CH2CN) 60.7 (d, J17.61 Hz, 1C,POCH2CH2CH2O) 67.3 (s, 1C, POCH2CH2CH2O) 71.1 (s, 1C, OCH2CH2CH2), 117.6 ppm (s,1C, CN). 3?P NMR (162 MHz, CDC13, ?H-decoupled) 8 147.56 ppm (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23377-40-4, its application will become more common.

Reference:
Patent; UNIVERSITY OF MASSACHUSETTS; UNIVERSITY OF SOUTHAMPTON; WATTS, Jonathan; HAITCHI, Hans, Michael; PENDERGRAFF, Hannah; (88 pag.)WO2018/226788; (2018); A1;,
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349-75-7, 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. 349-75-7, name is (3-(Trifluoromethyl)phenyl)methanol, molecular formula is C8H7F3O, 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.

10.1 Ethyl 6-trimethylsilyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxylate 0.52 ml (3.83 mmol) of 3-(trifluoromethyl)phenylmethanol and 0.92 g (3.83 mmol) of (cyanomethylene)tributylphosphorane (CMBP) are added, at ambient temperature, to a solution of 0.5 g (1.91 mmol) of ethyl 6-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 1.2, in 8 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is stirred at 110 C. for 15 hours and then concentrated to dryness. The reaction crude is subsequently purified by successive rounds of flash chromatography on a silica gel column, to give 0.72 g of expected ethyl 6-trimethylsilyl-1-[[(3-trifluoromethyl)phenyl]methyl]-1H-indole-2-carboxylate in the form of an oil. 1H NMR (DMSO D6), delta (ppm): 7.49-7.45 (m, 2H); 7.36-7.33 (m, 2H); 7.25 (t, 1H); 7.12 (s, 1H); 7.04-7.00 (m, 2H); 5.73 (s, 2H); 4.04 (q, 2H); 1.03 (t, 3H); 0.00 (s, 9H). LC-MS: 420 ([M+H]+, Rt=3.57).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 349-75-7, (3-(Trifluoromethyl)phenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2011/9365; (2011); A1;,
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