Month: March 2022

Synthetic Route of 1013031-65-6, 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 1013031-65-6, name is (2,6-Dibromophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

A Teflon reaction tube was charged with (2,6-dibromophenyl)methanol (1.00 g, 3.76 mmol) and DCM (10 mL). The solution was cooled to 00 C and DAST (0.55 mL, 4.1 mmol) was added. Themixture was stirred for 10 mm, then NaHCO3 (saturated solution, 10 mL) was added. The aqueous layer was extracted with DCM and the combined organics dried (MgSO4) and concentrated. The residue was purified by column chromatography (Si02, 0-30% EtOAc/hex) to yield 1,3-dibromo-2- (fluoromethyl)benzene.

According to the analysis of related databases, 1013031-65-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
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Application of 55977-10-1, 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. 55977-10-1, name is 3-Bromo-7-hydroxy-4-methylchromen-2-one, molecular formula is C10H7BrO3, 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 mixture of 3-bromo-7-hydroxy-4-methyl-2H-chromen-2-one (i) (7.66 g, 30 mmol), 4-(4-methylpiperazine-1-carbonyl)phenylboronic acid hydrochloride (2) (10.24 g, 36 mmol), Na3PO4(22.14 g, 135 mmol), ethoxyethanol (140 g) and water (14 g) was purged with Argon for five minutes in a 250 ml, pressure vessel. Ligand Sphos (obtained from Aldrich, Cat No. 638072) (739 mg, 1.8 mmol) and Pd(OAc)2(202 mg, 0.90 mmol) were added under an Argon atmosphere then the vessel was sealed and heated for 60 min in a 150 C. oil bath with strong stirring. This process was repeated once. Upon cooling, the reaction mixtures were filtered through a silica plug using CH2Cl2and MeOH wash. The unified solutions were evaporated to 100 mL slowly diluted with water (100 mL) and crystallized at 0 C. The product was filtered, washed with 50% MeOH (2×30 mL) and dried to afford 18.52 g (81%) of the title compound.

According to the analysis of related databases, 55977-10-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MANNKIND CORPORATION; ZENG, QINGPING; TORO, ANDRAS; PATTERSON, JOHN BRUCE; WADE, WARREN STANFIELD; ZUBOVICS, ZOLTAN; YANG, YUN; WU, ZHIPENG; (403 pag.)JP2015/214548; (2015); A;,
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Application of 626-95-9, 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. 626-95-9, name is 1,4-Pentanediol. A new synthetic method of this compound is introduced below.

Referential Example 2: 4-(t-Butyldiphenylsilyloxy)-1-methyl-1-butanol In N,N-dimethylformamide (200 ml) were dissolved 1,4-pentanediol (10.0 g, 96.0 mmol) and imidazole (6.6 g, 96.9 mmol).. Under ice cooling, t-butyl chlorodiphenylsilane (25.2 ml, 96.4 mmol) was added dropwise.. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 days.. To the reaction mixture was added diethyl ether, followed by washing with water.. The organic layer was dried over anhydrous magnesium sulfate.. After filtration, the residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (32.0 g, 97%) was obtained as a colorless oil. IR (ATR) nu: 3350, 2929, 2856, 1427, 1105, 822, 739, 698, 609, 501 cm-1.1H-NMR (400MHz, CDCl3) delta: 1.05(9H,S), 1.19(3H,d,J=6.3Hz), 1.46-1.72(4H,m), 2.02-2.08(1H,m), 3.69(2H,t,J=6.0Hz), 3.78-3.90(1H,m), 7.30-7.50(6H,m), 7.62-7.88(4H,m). MS (m/z): 343 (M++H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-95-9, 1,4-Pentanediol, and friends who are interested can also refer to it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 52221-92-8, 3-(2-Bromo-phenyl)-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, COA of Formula: C9H11BrO, blongs to alcohols-buliding-blocks compound. COA of Formula: C9H11BrO

EXAMPLES; EXAMPLE 1 : 3-(2-bromophenyl)propionaldehyde; Following the procedure described by Stambuli, JP. in J. Am. Chem. Soc. (2001 ), 123 (11 ), 2677-2678, for the reduction of 3-(4-bromophenyl)propionic acid, 3-(2-bromophenyl)propionic acid was reduced to 3-(2- bromophenyl)propan-1-ol using BH3 SMe2 in tetrahydrofurane. Then the alcohol was converted to the corresponding aldehyde following the procedure described by Cooke, MP. in J. Org. Chem. (1987), 52 (8), 1381 -1396.

The synthetic route of 52221-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FARMAPROJECTS, S. A.; WO2007/101841; (2007); A2;,
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Synthetic Route of 15963-47-0, 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.15963-47-0, name is (3-Chlorocyclobutyl)methanol, molecular formula is C5H9ClO, molecular weight is 120.58, as common compound, the synthetic route is as follows.

(A) [[(3-Chlorocyclobutyl)methoxy]methyl]benzene A mixture of 3-chlorocyclobutanemethanol (17.3 g, 0.143 mole) and benzylbromide (26.96 g, 0.158 mole) in dry dimethylformamide (123 ml) was stirred at room temperature under an argon atmosphere and a 60% suspension of sodium hydride (6.31 g 0.158 g mole) was added. The reaction was stirred at ambient temperature for 22.5 hours. The reaction mixture was poured into 600 ml of water and the aqueous mixture extracted with ethyl acetate (4*500 ml). The ethyl acetate extracts were combined and dried over anhydrous sodium sulfate and the ethyl acetate evaporated in vacuo yielding the crude product as a yellow oil. The material was purified on a 2-liter Merck silica gel column eluding with 3 liters of hexane, followed by 5% ethyl acetate/hexane. The fractions containing the desired product were combined and the volatiles evaporated in vacuo yielding 28.6 g of the title compound as a pale yellow oil.

Statistics shows that 15963-47-0 is playing an increasingly important role. we look forward to future research findings about (3-Chlorocyclobutyl)methanol.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4918075; (1990); A;,
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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. 5617-32-3, name is 3,6,9,12,15,18-Hexaoxaicosane-1,20-diol, the common compound, a new synthetic route is introduced below. SDS of cas: 5617-32-3

General procedure: (Using the synthesis of macrocyclic sulfate 6a as an example). To a stirring solution of tetra(ethylene glycol) 5a (40.0 g, 205.95 mmol), triethylamine (100.73 g, 988.56 mmol), and DMAP (1.26 g, 10.30 mmol) in CH2Cl2 (3 L) at 0 °C was slowly added a solution of SOCl2 (50.30 g, 411.90 mmol, in 50 mL CH2Cl2). After the addition, the stirring mixture was warmed to 25 °C and monitored with TLC until the complete consumption of tetra(ethylene glycol). The reaction was quenched with 1.5 L water. The organic layer was collected, filtrated through a pad of silica gel, and concentrated under vacuum to provide the macrocyclic sulfite intermediate as brownish oil which was used directly in the next step. To the solution of macrocyclic sulfite in a mixture of CH2Cl2 (200 mL), CH3CN (200 mL), and water (300 mL) at 0 °C was added NaIO4 (52.86 g, 247.14 mmol) and RuCl3?3H2O (0.27 g, 1.03 mmol). The stirring mixture was gradually warmed to 25 °C and monitored with TLC. Upon complete consumption of the macrocyclic sulfite, the reaction mixture was filtered through a pad of Celite. Organic layer was collected, washed with brine, concentrated under vacuum, and recrystallized in methanol at -20 °C to afford the macrocyclic sulfate 6a as clear crystal (25.14 g, 47percent yield).

The synthetic route of 5617-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deng, Tao; Mao, Xianglan; Xiao, Yan; Yang, Zhigang; Zheng, Xing; Jiang, Zhong-Xing; Bioorganic and Medicinal Chemistry Letters; vol. 29; 4; (2019); p. 581 – 584;,
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Related Products of 13588-28-8, 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 13588-28-8, name is 2-(2-Methoxypropoxy)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

Jimroth type reflux condenser, Dean-Stark trap tube,In a 100 mL two-necked flask equipped with a nitrogen inlet tube,Dipropylene glycol monomethyl ether represented by the following formula (20) (with isomer) (7.41 g, 50 mmol), vinylacetic acid synthesized in Example 1 (formula (1-0),4.74 g, 55 mmol),p-Toluenesulfonic acid monohydrate (0.48 g, 2.5 mmol)And toluene (35 mL) was added.Immerse the two-necked flask in an oil bath,The temperature of the oil bath was raised to 130 C.While maintaining the same temperature, the mixture was stirred for 4 hours under a nitrogen stream to distill off the by-produced water.Cool the two-necked flask to room temperature (25 C),Wash twice with 5 wt% aqueous sodium bicarbonate (10 mL),Further, after washing twice with distilled water (10 mL), it was dried over magnesium sulfate. After removing the magnesium sulfate, the solution was concentrated under reduced pressure in the same manner as in Example 2. The obtained concentrated residue was purified by distillation under reduced pressure to isolate the compound (1-1b) (10.57 g, yield 98%)

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 13588-28-8, 2-(2-Methoxypropoxy)propan-1-ol.

Reference:
Patent; JNC Corporation; Masayuki, Sato; Urata, Yasuo; Yatsuda, Shinichi; Masuhara, Shigeo; Hashimoto, Kazuki; (20 pag.)JP5803424; (2015); B2;,
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Synthetic Route of 6214-45-5 ,Some common heterocyclic compound, 6214-45-5, molecular formula is C11H16O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: In a 5 mL sealed tube, TBPB(30 mol%, 0.041 g), and TBHP (70 wt% in H2O, 1.0 mmol, 0.131 g) was added to a solution ofbenzyl alcohol 1a (0.4 mmol, 0.043 g) in chlorobenzene (1 mL). The resultant mixture washeated at 80 C for 2.5 h. After completion of the reaction as was indicated by TLC monitoring,the reaction mixture was cooled to ambient temperature and saturated NaHCO3 (2 mL) wasadded. The product was extracted with ethyl acetate (2 × 3 mL). The combined organic phasewas dried over Na2SO4. The solvent was removed under the reduced pressure. The residue waspurified by column chromatography using n-hexane-EtOAc (15:1) as eluent to afford pureproduct 2a as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6214-45-5, its application will become more common.

Reference:
Article; Adib, Mehdi; Pashazadeh, Rahim; Synlett; vol. 29; 1; (2018); p. 136 – 140;,
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Adding a certain compound to certain chemical reactions, such as: 69393-72-2, Benzo[d][1,3]dioxol-4-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, COA of Formula: C7H6O3, blongs to alcohols-buliding-blocks compound. COA of Formula: C7H6O3

a) 4-hydroxy-5-(4-propylpiperazinylmethyl)-1,3-benzodioxole Aqueous formaldehyde (37%; 3.67 g, 45.3 mmol) was added dropwise to a stirred solution of 4-hydroxy-1,3-benzodioxole (5.2 g, 37.8 mmol) and N-propylpiperazine (5.8 g, 45.3 mmol) in acetonitrile (25 ml). The reaction mixture was stirred at room temperature for one hour and evaporated in vacuo. The remaining oil (13.0 g) was purified chromatographically (with ethylacetate/methanol=9/1 (v/v) as an eluent to give 4-hydroxy-5-(4-propylpiperazinylmethyl)-1,3-benzodioxole (5.9 g, 56% yield; compound No. 25), m.p. 115-117 C.

The synthetic route of 69393-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duphar International Research B.V.; US5281595; (1994); A;,
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Application of 61266-36-2, 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. 61266-36-2, name is Methyl 4-(3-hydroxyprop-1-yn-1-yl)benzoate, molecular formula is C11H10O3, 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.

B. Preparation of methyl 4-(3-hydroxypropyl)benzoate STR17 To a 2-L stainless steel Parr bottle was charged 17.1 g (89.9 mmol) of methyl 4-(3-hydroxypropynyl)benzoate dissolved in 1 L MeOH, followed by the addition of 2.6 g of 5% Pd/C catalyst. This mixture was then hydrogenated at ambient temperature for 18 hours on a Parr shaker at 15 psi of hydrogen gas. The catalyst was filtered away, and washed with fresh MeOH. The filtrate was removed in vacuo, and the crude residue was flash chromatographed on silica gel eluding with 25% EtOAc/MeCl2. The correct fractions were combined and the solvents were removed in vacuo to give 16.7 g (95%) of methyl 4-(3-hydroxypropyl)benzoate as a colorless oil. Rf =0.36 (25% EtOAc/MeCl2) Mass (FD) M+=194 IR (KBr, cm-1)=1020, 1046, 1114, 1181, 1194, 1247, 1312, 1416, 1437, 1611, 1718, 2953, 3011, 3026, 3626 UV (EtOH) lambdamax =265, 203 (epsilon=25179, 16144) Anal. Calcd. for C11 H14 O3: C, 68.02; H, 7.27. Found: C, 67.95;H, 6.97. 1 H NMR (300 MHz, CDCl3) delta1.32 (t, J=5.5 Hz, 1H), 1.88-197 (m, 2H), 2.79 (t, J=7.7 Hz, 2H), 3.70 (q, J=6.1 Hz, 2H), 3.92 (s, 3H), 7.29 (d, J=8.0 Hz, 2H), 7.98 (d, J=8.2 Hz, 2H)

According to the analysis of related databases, 61266-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US5426110; (1995); A;,
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