Tag: M.W=100-200

Electric Literature of 1875-88-3, 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. 1875-88-3, name is 2-(4-Chlorophenyl)ethanol, molecular formula is C8H9ClO, 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.

In a 1 L pressure vessel, 4-chlorophenylethanol (412.8 g, 2636 mmol) was stirred and heated to an internal temperature of -91 0C. The system was held under reduced pressure (~ – 0.98 bar) for ~2 min. Hydrogen bromide gas was gradually charged into the pressure vessel and the reaction was stirred at an internal pressure between +0.69 and +1.65 bar for 135 min. The vessel was allowed to slowly vent to a caustic scrubber and flushed with nitrogen gas for ~ 5 min. Conversion to the bromide was found to be 4.27% by HPLC. The reaction mixture was allowed to cool to ambient temperature overnight under nitrogen. The mixture was then heated once more in an oil bath set at 96 0C and the vessel was evacuated. The vessel was gradually filled with hydrogen bromide gas and stirred at an internal pressure between +1.38 and +1.65 bar for 2 h. Conversion to the bromide was found to be 92.67 % by HPLC. The reaction was held at a bath temperature of 96 0C at atmospheric pressure for 45 min. The vessel was then evacuated and slowly backfilled with hydrogen bromide gas over 15 min to +1.38 bar. After stirring for a further 2.5 h at +1.24 to +1.38 bar, the vessel was vented to the caustic scrubber and held at a bath temperature of 96 0C in closed system at atmospheric pressure. Conversion to the bromide was found to be 99.49% by HPLC with a peak area purity of 98.71%.In order to test stability and impurity formation, the pressure vessel was then evacuated and gradually back filled with hydrogen bromide gas to an internal pressure of +1.03 bar. The dark brown suspension was allowed to stir at +1.03 bar at a bath temperature of 96 0C. After 15 h the internal pressure had risen to +2.41 bar and the vessel was vented to the caustic scrubber, purged with nitrogen, and allowed to cool to ambient temperature. The peak area purity was found to be 96.06%. The reaction mixture was transferred to a seperatory funnel and allowed to separate at room temp. The upper product phase was washed with water (412 mL) in 2 portions to leave a milky beige suspension (563.4 g) with an HPLC peak area purity of 99.29%.

According to the analysis of related databases, 1875-88-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/111004; (2009); A1;,
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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. 769-30-2, name is Benzo[d][1,3]dioxol-4-ylmethanol, molecular formula is C8H8O3, 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. Formula: C8H8O3

Benzo[d][1,3]dioxo-4-ylmethanol (223 mg, 1.47 mmol)Dissolved in dichloromethane (10 mL), then phosphorus tribromide (0.17 mL, 1.8 mmol) was added dropwise at 0 C.After the completion of the dropwise addition, the mixture was stirred at room temperature for 3 hours.The reaction was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (50 Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 456-47-3, 3-Fluorobenzyl alcohol, 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: C7H7FO, blongs to alcohols-buliding-blocks compound. COA of Formula: C7H7FO

Aniline (46.5 mg, 0.5 mmol),Cat.[Ir] (5.4 mg, 0.005 mmol, 1 mol%), cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.),3-Fluorobenzyl alcohol (75.6 mg, 0.6 mmol) and t-amyl alcohol (1 ml) were sequentially added to a 5 mL round-bottomed flask.The reaction mixture was refluxed in air for 12 hours and then cooled to room temperature.The solvent is removed by rotary evaporation and then passed through column chromatography (developer:Petroleum ether/ethyl acetate gives the pure target compound, yield: 95%.

The synthetic route of 456-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Science and Technology; Fan Hongjun; Li Shun; Liu Pengcheng; Li Feng; (9 pag.)CN107778182; (2018); A;,
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Related Products of 10488-69-4, Adding some certain compound to certain chemical reactions, such as: 10488-69-4, name is Ethyl 4-chloro-3-hydroxybutanoate,molecular formula is C6H11ClO3, 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 10488-69-4.

A solution of 8.26 g of glycine, 12.2 g of sodium carbonate, 0.85 g of catalyst 1,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) was added to 200 mL of tetrahydrofuran and stirred at 40-50 ¡ã C ,16.7 g (100 mol) of ethyl (S) -3-hydroxy-4-chlorobutyrate dissolved in 50 mL of tetrahydrofuran was slowly added,After dripping,After maintaining the reaction at 48 ¡ã C for 0.5 hour,The temperature was raised to 77 ¡ã C to continue the reaction for 5 hours,After completion of the reaction, the reaction solution was cooled to room temperature,Filter out insoluble matter,Vacuum recovery of most of the organic solvent recovery,Add water to the residue,Sodium hydroxide solution to adjust the reaction solution pH to 8.5,Extracted with ethyl acetate,Water dilute hydrochloric acid to adjust the pH to 1.6,Ethyl acetate extraction,Dried and concentrated to 14.9 g of a white solid (S) -4-hydroxy-2-oxo-1-pyrrolidine acetic acid,Yield 93.6percent (calculated as ethyl (S) -3-hydroxy-4-chlorobutyric acid ethyl ester)HPLC purity 95.80percent (area normalization).

According to the analysis of related databases, 10488-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Murderson Biopharmaceutical Co., LTd.; Li, Zhongjun; Han, Bo; Niu, Huaying; Liu, Fanlei; (10 pag.)CN106397294; (2017); A;,
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Reference of 37585-16-3, 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 37585-16-3, name is (2-Amino-4-chlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of (2-amino-4-chlorophenyl)methanol (5.9 g) in ethyl acetate (100 ml_) was heated until the former dissolved. Acetic anhydride (8 ml_) was added and the mixture removed from the heat. The precipitate was filtered to give a white solid and the filtrate was concentrated and slurried with hexane and filtered to give further white solid. The two batches were combined to give 5.3 g of the alcohol intermediate. The first phase of the experiment was repeated on 3x the scale described above. 21 g of the combined products was dissolved in DCM (65OmL) and added to a solution of thionyl chloride (23 ml_) in DCM (225 ml_) at room temperature under argon. The mixture was stirred for 30 minutes and concentrated to give a yellow/red solid. The solid was dissolved in DCM (500 ml_), washed with saturated sodium bicarbonate (200 ml_) and dried over magnesium sulfate. Removal of the solvent gave the 22 g of the title compound as a yellow/brown solid. 1H NMR (CDCI3) delta 8.01 (d, 1 H), 7.52 (br. s, 1 H), 7.23 (d, 1 H), 7.12 (dd, 1 H), 4.58 (s, 2H), 2.25 (s, 3H).

According to the analysis of related databases, 37585-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMTED; WO2007/14054; (2007); A2;,
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Electric Literature of 116-02-9 ,Some common heterocyclic compound, 116-02-9, molecular formula is C9H18O, 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.

Synthesis 4 Synthesis of 3-(3,3,5-trimethylcyclohexyloxy)phenol In a four necked flask (1 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (42 g, 0.38 mol), 3,3,5-trimethylcyclohexanol (54 g, 0.57 mol) and triphenylphosphine (150 g, 0.57 mol) were dissolved in dried tetrahydrofuran (200 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (100 g, 0.5 mol) and dried tetrahydrofuran (150 ml) was dropped for 1 hour while cooling with an iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30 % hydrogen peroxide (75 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-4A) (19.5 g, 22 % yield, 99 % GC purity). The chemical shift value (delta ppm, TMS standard) of 1H-NMR of this compound in a heavy dimethyl sulfoxide solvent was 0.7 (m, 1H), 0.9 to 1.0 (m, 9H), 1.2 to 2.0 (m, 6H), 4.1 (m, H), 6.5 (m, 3H), 7.0 (m, H), 8.9 (b, H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116-02-9, its application will become more common.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP2505576; (2012); A1;,
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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. 2240-88-2, name is 3,3,3-Trifluoropropan-1-ol, molecular formula is C3H5F3O, 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. Safety of 3,3,3-Trifluoropropan-1-ol

A solution of DIAD (0.743 mL, 3.82 mmol) in THF (2.00 mL) was added slowly to a solution of 4-fluoro-3-nitrophenol (500 mg, 3.18 mmol), 3,3,3-trifluoropropan-l-ol (0.310 mL, 3.50 mmol) and PPli3 (1.00 g, 3.82 mmol) in THF (10.0 mL). The resulting reaction mixture was allowed to stir at RT overnight, after which TLC (20percent EtOAc in Hex) and LC-MS analysis showed product formation. Reaction mixture was concentrated under reduced pressure and residue purified by flash column chromatography: silica gel with a gradient of 5-20percent EtOAc in Hex to afford l-fluoro-2-nitro-4-(3,3,3-trifluoropropoxy)benzene (322 mg, 40.0 percent yield) as a clear golden oil. NMR (400 MHz, DMSO-ifc) d 7.68 (dd, J= 6.0, 3.2 Hz, 1H), 7.54 (dd, J= 10.9, 9.2 Hz, 1H), 7.42 (dt, J = 9.3, 3.5 Hz, 1H), 4.31 (t, .7= 5.9 Hz, 2H), 2.8l (qt, /= 11.4, 5.9 Hz, 2H). 19F NMR (376 MHz, DMSO-ifc) d -63.06 (t, J= 11.2 Hz, 3F), -129.28 (ddd, J= 10.3, 6.0, 3.6 Hz, IF). LCMS RT (Method 2) = 3.491 min.

With the rapid development of chemical substances, we look forward to future research findings about 2240-88-2.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; PONTIFICIA UNIVERSIDAD CATOLICA DE CHILE; SOUTHALL, Noel T.; VON BERNHARDI, Rommy M.; ALVAREZ, Alejandra; DEXTRAS, Christopher R.; DULCEY, Andres E.; MARUGAN, Juan J.; ZANLUNGO, Silvana; TALLEY, Daniel C.; FERRER, Marc; HU, Xin; (0 pag.)WO2019/173761; (2019); A1;,
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Electric Literature of 100-37-8 ,Some common heterocyclic compound, 100-37-8, molecular formula is C6H15NO, 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: An oven dried 10 mL round bottom flask equipped with a stir bar was brought into the glove box with a reflux condenser. The flask was charged with [RuHCl(CO)(HN(CH2CH2PPh2)2)] (4) (6.0 mg, 0.01 mmol, 1mol%), KOH (8.2 mg, 0.15 mmol, 15mol%), toluene (1.0mL), an amine (1 mmol, 1.0 equiv), and an alcohol (1mmol, 1.0equiv) in that order. After all reagents have been added to the flask, the reflux condenser was attached and secured with a Keck clamp. The top of the condenser was sealed with a septum and the whole apparatus was then removed from the glove box. Once outside the glove box, the apparatus was equipped to nitrogen flow by inserting an inlet needle supplying a positive pressure of nitrogen into the septum, and an outlet needle connected to an oil bubbler. The reaction mixture was heated at reflux in a silicone oil bath overnight (12h), then allowed to cool to rt, and the conversion determined by GC-MS (CI). The resulting residue was subjected to flash chromatography with the indicated solvent system to obtain the purified amide in the reported isolated yield.

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. 100-37-8, 2-(Diethylamino)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Oldenhuis, Nathan J.; Dong, Vy M.; Guan, Zhibin; Tetrahedron; vol. 70; 27-28; (2014); p. 4213 – 4218;,
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Adding a certain compound to certain chemical reactions, such as: 558-42-9, 1-Chloro-2-methyl-2-propanol, 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, Product Details of 558-42-9, blongs to alcohols-buliding-blocks compound. Product Details of 558-42-9

To a suspension of I-47 (336 mg, 0.93 mmol) and potassium carbonate (154 mg, 1.12 mmol) in DMF (6 mL) is added 1-chloro-2-methyl-propan-2-ol (100 muL, 0.98 mmol). The reaction mixture is stirred at 80¡ã C. for 16 h then concentrated in vacuo. The residue is extracted with CH2Cl2, washed with saturated aqueous NH4Cl, dried with Na2SO4, filtered and concentrated in vacuo to afford I-104 (365 mg); m/z 434 [M+H].

The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
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Reference of 3068-00-6, 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.3068-00-6, name is 1,2,4-Butanetriol, molecular formula is C4H10O3, molecular weight is 106.1204, as common compound, the synthetic route is as follows.

General procedure: Xantphos (28.9 mg, 0.05 mmol), Cs2CO3 (32.6 mg, 0.10 mmol) and [Ru(p-cymene)Cl2]2 (15.3 mg, 0.025 mmol) were added to a Schlenk tube. Then the tube was evacuated and refilled with nitrogen. Dry toluene as solvent (2.0 mL)were added and the solution was stirred at room temperature under nitrogen for 30 min. Activated molecular sieves 4A (0.10 g) and triol 6a (106.1 mg, 1.00 mmol) were then added. And the solution was stirred at room temperature under nitrogen for 40 min. Subsequently, aniline 5a (46.6 mg, 0.50 mmol) was added and the solution was stirred at room temperature under nitrogen for 20 min. Then the resulting solution was heated to reflux and stirred for 48 h. The reaction was monitored by TLC. After completion, the solution was filtered through a plug of Celite and washed with EtOAc (3 mL x 3). The filtrate was concentrated under vacuum. Purification via flash column chromatography with silica gel (eluting with PE/EA = 5/1 (v/v)) yielded 4a (43.0 mg, 81% yield) as light yellow oil.

Statistics shows that 3068-00-6 is playing an increasingly important role. we look forward to future research findings about 1,2,4-Butanetriol.

Reference:
Article; Xu, Qing-Song; Li, Chen; Xu, Yong; Xu, Defeng; Shen, Mei-Hua; Xu, Hua-Dong; Chinese Chemical Letters; (2019);,
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