Author: tianli

Adding a certain compound to certain chemical reactions, such as: 27129-87-9, (3,5-Dimethylphenyl)methanol, 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: C9H12O, blongs to alcohols-buliding-blocks compound. COA of Formula: C9H12O

Step 1 1-(2-Aminoethyl)-3-(3,5-dimethylbenzyl)-2-imidazolidinylidenepropanedinitrile (Compound (IXa)): 1-(2-Aminoethyl)-2-imidazolidinylidenepropanedinitrile (9.7 g) obtained by a known process (JP92-279581), 5.0 g of 3,5-dimethylbenzyl alcohol, 12 g of triphenylphosphine, and 10 g of di-tert-butyl azodicarboxylate were allowed to react in 500 ml of tetrahydrofuran as described in Example 23 to give 3.6 g (34%) of Compound (IXa) as a pale yellow oily substance. 1H NMR (270 MHz, CDCl3) delta: 6.89 (1H, s), 6.81 (2H, s), 4.62 (2H, s), 3.62-3.55 (4H, m), 3.42-3.34 (2H, m), 2.98 (2H, t), 2.25 (6H, s). The signal which corresponds to primary amine was not observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27129-87-9, (3,5-Dimethylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; Kyowa Hakko Kogyo Co., Ltd.; US6469002; (2002); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 486460-26-8, 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 486460-26-8, name is (4-Bromo-2,5-difluorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

NaH (210 mg, 8.8 mmol) was added to a solution of XLVII-3 (446 m g, 2 mmol) in DMF (10 mL) at 0 C. The reaction mixture was stirred at 0 C. for 30 mins. A solution of XLVII-3A (366 mg, 2 mmol) in DMF (5 mL) was added dropwise. The reaction mixture was stirred at 0 C. for 4 h. Water (5 mL) was added. The reaction mixture was diluted with brine and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by column (PE/EA=2/1) to afford XLVII-4 (200 mg, yield 30.7%).

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 486460-26-8, (4-Bromo-2,5-difluorophenyl)methanol.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/200215; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 110-73-6 ,Some common heterocyclic compound, 110-73-6, molecular formula is C4H11NO, 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.

In 100mL 1-neck round bottom flask[A-1] (Benzenesulfonate Dichlorosulfofluorescein) (3 g, 7.40 mmol, 1 eq), [A-2] (2-(Ethylamino)ethanol) (5.28g, 59.22mmol, 8eq) and 50 g of DI-water were added thereto, followed by stirring at 100 C. Then stirred for 20 hours. The reaction was terminated by quenching in 1M HCl Solution, and the reaction was precipitated by the addition of sodium chloride (NaCl).The resulting precipitate was filtered under reduced pressure and dried at 80 C Oven. After drying, the resultant was dissolved in DMF (Dimethylformamide) to remove NaCl between the products, filtered, and the filtrate was quenched with diethyl ether, filtered under reduced pressure, and dried to obtain Compound [A] (2.98 g, 5.84 mmol, 78.9%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,110-73-6, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Lee Da-mi; Choi Sang-a; Yang Seung-jin; Lee Jae-yong; Kim Hye-jin; Kim Ji-seon; Kim Yeong-ung; Park Jong-ho; (27 pag.)KR2020/7157; (2020); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3236-48-4, trans-1,4-Cyclohexanedimethanol, 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, Safety of trans-1,4-Cyclohexanedimethanol, blongs to alcohols-buliding-blocks compound. Safety of trans-1,4-Cyclohexanedimethanol

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3236-48-4, trans-1,4-Cyclohexanedimethanol, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 41175-50-2 , The common heterocyclic compound, 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, 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.

To a solution of aldehyde 7 (300 mg, 0.428 mmol) in propionic acid (5 mL) was added 8-hydroxyjulolidine (161 mg, 0.856 mmol, 2 eq) and PTSA (8 mg, 0.042 mmol, 0.1 eq). The solution was protected from light and stirred at room temperature overnight. To the brown mixture was added a solution of chloranil (103 mg, 0.428 mmol, 1 eq) in DCM (10 mL), the reaction turned dark and was allowed to stir overnight at room temperature. The dark purple solution was evaporated to dryness. The residue was purified by column chromatography on silica gel (gradient of 100% DCM to 9/1 DCM/Methanol) to obtain 130 mg of 8 (30%) as a purple solid after lyophilisation (dioxane/water: 1/1). Rf=0.32 (DCM/MeOH, 9/1). 1H-NMR (300 MHz, CDCl3): delta 7.84 (d, J = 8.1 Hz, 1H, H Ar), 7.06 (d, J = 7.9, 1H, H Ar), 6.97-6.86 (m, 5H, H Ar, H7), 6.71 (d, J = 2.9 Hz, 1H, H Ar), 4.47-4.40 (m, 4H, CH2O), 4.21 (s, 4H, NCH2COOMe), 4.11 (s, 4H, NCH2COOMe), 3.87 (t, J = 6.1 Hz, 2H, CH2O), 3.67 (s, 6H, 2 OMe), 3.56 (m, 14H, 2 OMe, H1, H4), 3.11 (d, J = 7.0 Hz, 2H, CH2N3), 3.04 (t, J = 6.3 Hz, 4H, H6), 2.75 (q, J = 6.2 Hz, 4H, H3), 2.13-2.10 (m, 4H, H5), 2.00 (t, J = 5.5 Hz, 4H, H2), 1.49-1.34 (m, 4H, CH2), 1.19-1.03 (m, 4H, CH2). 13C-NMR (75 MHz, CDCl3): delta 171.97 (CO ester), 171.56 (CO ester), 153.04 (C Ar), 152.74 (C Ar), 152.31 (C Ar), 152.09 (C Ar), 151.02 (C Ar), 150.43 (C Ar), 144.79 (C Ar), 139.41 (C Ar), 138.16 (C Ar), 132.61 (C Ar), 128.20 (CH Ar), 127.15 (CH Ar), 126.33 (CH Ar), 123.34 (C Ar), 122.64 (CH Ar), 122.61 (CH Ar), 121.91 (CH Ar), 119.54 (CH Ar), 113.89 (C Ar) (CH Ar), 113.43 (C Ar), 113.35 (C Ar), 105.16 (C Ar), 69.10 (CH2O), 67.70 (CH2O), 67.19 (CH2O), 53.66 (NCH2COOMe), 53.52 (NCH2COOMe), 51.73 (4 OMe), 51.16 (CH2N3), 50.97 (C1 or C4), 50.52 (C1 or C4), 28.82 (CH2), 28.73 (CH2), 27.72 (C3), 26.26 (CH2), 25.52 (CH2), 20.83 (C2), 20.00 (C6), 19.85 (C5). MS (ES+), calcd for C57H68N7O12 [M]+ 1042.5, found 1042.9. HRMS (ES+), calcd for C57H68N7O12 [M]+ 1042.4920, found 1042.4949.

The synthetic route of 41175-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Paris Sciences et Lettres – Quartier Latin; Mallet, Jean-Maurice; Collot, Mayeul; EP2878602; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 4415-82-1, 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 4415-82-1 as follows.

To a suspension of sodium hydride (60% dispersion in mineral oil, 37 mg, 0.93 mmol) in THF (1 mL) was added cyclobutanemethanol (86 mu^, 0.91 mmol) at room temperature. A solution of compound 94 (200 mg, 0.46 mmol) in THF (3.5 mL) was added at room temperature. The mixture was stirred at room temperature for 30 min, at 50 C for 2 h, and cooled to room temperature. Aq. sat. NaHCCb was added. The mixture was extracted with EtOAc. The organic extract was dried withNa2SC>4, and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 50% EtOAc in hexanes) to give compound 213 (203 mg, 91 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-82-1, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, molecular formula is C10H12O3, 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. Computed Properties of C10H12O3

Step 6 (2R)-2-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxy]3-phenyl-propionic acid methyl ester To a solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenol (5.0 g, 12.1 mmol), (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (3.3 g, 18.3 mmol), and triphenylphosphine (4.8 g, 18.3 mmol) in anhydrous benzene (50 mL) at room temperature under nitrogen was added dropwise diethyl azodicarboxylate (2.6 mL, 18.3 mmol) over a period of 25 min. The reaction mixture was heated for 2 h, then stirred at room temperature for 3 days. The crude reaction mixture was adsorbed onto silica gel and chromatographed twice with petroleum ether:ethyl acetate (95:5) to yield the title compound as a white foamy solid (4.5 g, 65%): NMR (DMSO-d6): delta8.18 (d, 1H), 7.64 (ddd, 1H), 7.53-7.43 (m, 2H), 7.38-7.24 (m, 5H), 7.00 (s, 2H), 4.80 (t, 1H), 3.58 (s, 3H), 3.31 (m, 2H), 2.42 (s, 3H), 2.24 (s, 3H), 2.19 (s, 3H), 1.55 (s, 3H); MS(EI): [M+], 1 bromine isotope pattern, 572/574; Anal. Calc. for C32H29BrO3S: C, 67.01; H, 5.10; N, 0.00. Found: C, 66.33; H, 5.09; N, 0.09; Analytical HPLC indicates a major component (94.39%).

With the rapid development of chemical substances, we look forward to future research findings about 13674-16-3.

Reference:
Patent; American Home Products Corporation; US6251936; (2001); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 83647-43-2, 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 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Dioxane (200 mL) was charged to a 500 mL round-bottom flask and nitrogen was bubbled through for 10 minutes. (3-bromo-2-methylphenyl)methanol (9.0 g, 44.8 mmol) was added and nitrogen was bubbled through for 10 minutes. Potassium acetate (13.18 g, 134 mmol) was added and nitrogen was bubbled through for 10 minutes. Bis(pinacolato)diboron (18.19 g, 71.6 mmol) was added and nitrogen was bubbled through for 10 minutes. PdCl2(dppf)-CH2Cl2 (4.75 g, 5.82 mmol) was added and nitrogen was bubbled through for 10 minutes. The reaction was heated at 80 C overnight. The reaction was diluted with ethyl acetate (200 ml) , filtered through a celite bed and the bed washed with ethyl acetate. The combined organic portions were concentrated under vacuum to provide a black pasty residue. This crude residue was adsorbed onto silica gel and chromatographed on a 120 g silica gel column using acetone in petroleum ether. The product eluted at 5.0 % acetone. Fractions containing the product were combined and the solvent was removed under vacuum. An off-white solid was obtained. The solid was stirred with petroleum ether and filtered under vacuum to remove boron impurities. The title compound (8.7g, 77%) was pure by NMR analysis. 1H NMR (500MHz, DMSO-de) delta 7.33 (dd, J=0.9, 7.5 Hz, 1H), 7.45 (d, J=6.9 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 4.73 (d, J=3.0 Hz, 2H), 2.58 (s, 3H), 1.58 (br. s., 1H, OH), 1.37 (s, 12H).

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 83647-43-2, (3-Bromo-2-methylphenyl)methanol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHUPAK, Louis S.; ZHENG, Xiaofan; WO2015/34820; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 480449-99-8, 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. 480449-99-8, name is Benzyl 3-hydroxycyclobutanecarboxylate. A new synthetic method of this compound is introduced below.

REFERENTIAL EXAMPLE 153 Benzyl 3-methoxycyclobutanecarboxylate: Methyl iodide (194 mul) and silver oxide (237 mg) were added to a solution of the compound (317 mg) obtained in Referential Example 151 in N,N-dimethylformamide (3.0 ml), and the mixture was stirred at 45 C. for 1 hour. Methyl iodide (194 mul) and silver oxide (226 mg) were additionally added to the reaction mixture, and the mixture was stirred at 45 C. for 16 hours. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate_hexane=1:10) to obtain the title compound (152 mg). 1H-NMR (CDCl3) delta: 2.14-2.24(2H,m), 2.44-2.54(2H,m), 2.59-2.72(1H,m), 3.21(3H,s), 3.73-3.81(1H,m), 5.11(2H,s), 7.22-7.39(5H,m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,480449-99-8, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (2005); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 25392-41-0, 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

The crude product (2 g, 9.50 mmol) in 200 mL single neck flask, adding 1 n naoh (100ml) the concentrated solution immediately turned yellow, and the solution was placed in an oil bath and heated to reflux for 2 h, and after the reaction, cooling to room temperature, with concentrated sulfuric acid to adjust the pH to 2 -3, and the resulting solution with ethyl acetate (30 ml × 4) the extraction, combining the organic phase with saturated saline (20 ml × 2, washed, dried over anhydrous sodium sulfate, filtered Solvent, the filtrate is evaporated under reduced pressure to obtain gray-brown columnar crystalline 1.3 g, the crude yield 71.2% of the crude product (1 g, 5.20 mmol) suspended in 10 mL of methanol and added dropwise 0 5 Ml of concentrated sulfuric acid, after dropping, heating under reflux to react for about 4 h, after the reaction, the methanol was removed under reduced pressure, the residual liquid is poured into 30 ml of water, in ethyl acetate (20 ml × 3) extraction, combining the organic phase with saturated sodium bicarbonate solution (15 mL × 2) washing, saturated brine (15 mL × 2, washed, dried over anhydrous sodium sulfate, filtered, the filtrate is decompressed and evaporated to obtain an yellow-brown oil, column chromatography (petroleum ether/ethyl acetate, 80: 20 Purification, v/v) to obtain light yellow solid 0.75 g, 70% yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25392-41-0, 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; ChinaPharmaceutical University; Huang, Wenlong; QIAN, Hai; Li, Zheng; YANG, Jianyong; Su, Xin; Pan, MiaoBo; (22 pag.)CN105566267; (2016); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts