* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0333333 h; Stage #2: at 80℃; for 4 h;
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 ml_) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 ml_, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 ml_) and extracted with EtOAc (2 x 100 ml_). The combined organic layer was washed with brine solution (50 ml_), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4- chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. 1H NMR (400 MHz, CDC ): δ ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
96.5%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0333333 h; Stage #2: at 80℃; for 4 h;
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 mL) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv ) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 mL, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. NMR (400 MHz, CDCI3): δ ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
90%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24 h;
General procedure: To a stirred solution of phenol (1 mmol) in DMF (3 mL) were added methyl bromoacetate (0.1 mL, 1 mmol) and K2CO3 (207 mg, 1.5 mmol), and the resulting mixture was heated at 80 °C for 24 h. After cooling, the reaction mixture was diluted with EtOAc, and filtered by celite pad. The filtrate was evaporated, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 50 : 1 ~ 40 : 1) to give corresponding ether.
Reference：
[1] Patent: WO2017/212423, 2017, A1, . Location in patent: Page/Page column 71; 72
[2] Patent: WO2017/212425, 2017, A1, . Location in patent: Page/Page column 68-69
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735
[4] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12096 - 12099
[5] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5492 - 5500
2
[ 96-34-4 ]
[ 106-48-9 ]
[ 4841-22-9 ]
Reference：
[1] Synthetic Communications, 2005, vol. 35, # 13, p. 1759 - 1764
[2] Synthetic Communications, 1984, vol. 14, # 1, p. 69 - 76
[3] Journal of Chemical Research, 2005, # 7, p. 432 - 433
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 5, p. 1312 - 1314
[5] Journal of Chemical Research, 2010, # 8, p. 452 - 454
[6] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 5, p. 974 - 980
[7] Molecules, 2017, vol. 22, # 1,
3
[ 67-56-1 ]
[ 122-88-3 ]
[ 4841-22-9 ]
Reference：
[1] Synthetic Communications, 2004, vol. 34, # 3, p. 377 - 382
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 7, p. 629 - 631
[3] Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1082 - 1083
[4] Journal of the Chemical Society, 1922, vol. 121, p. 1603
[5] Synthetic Communications, 2008, vol. 38, # 23, p. 4107 - 4115
4
[ 67-56-1 ]
[ 51-68-3 ]
[ 4841-22-9 ]
Reference：
[1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 3, p. 779 - 782
With hydrazine hydrate; In ethanol; for 6h;Reflux;
General procedure: To an oven-dried round bottomed flask with a stirring bar was added a solution of substituted phenol (0.01 mol, 1 eq.) and K2CO3 (1.2 eq.) in 50 mL of dry DMF. Excess ethyl chloroacetate dissolved in 10 mL of DMF was then slowly added through a dropping funnel to the above solution.The resulting mixture was stirred at 90 C for 5-6 h. The reaction was quenched with saturated NaCl solution, then extracted with dichloromethane(DCM), washed with brine, dried over MgSO4 and then concentrated on a rotary evaporator affording methyl 2-phenoxyacetate 1 (80%-95% yield) which was used for the next step without further purification [17].This product 1 (0.009 mol, 1 eq.) wasdissolved in 30 mL of ethanol and then placed in a round-bottomed flask equipped with a stirring bar; 80% of hydrazine hydrate (0.018 mol, 2 eq.) was slowly added to this mixture at room temperature through a dropping funnel. The resulting solution was heated up to reflux temperature and stirring was continued under this condition for another 6 h. The reaction mixture was filtered through celite,the filtrate was washed with brine, dried over MgSO4, and then concentrated in vacuo. The crudephenoxyacetohydrazide 2 was used directly without further purification in the next step.
With sodium hydroxide; In ethanol; water; at 0℃; for 2.5h;Reflux;
To a solution of methyl 2-(4-chlorophenoxy)acetate (22.5 g, 1 12.15 mmol) in ethanol (100 ml_) at 0 C was added a solution of sodium hydroxide (5.38 g, 134.58 mmol) in water (10 ml_). After stirring for 5 minutes at 0 C, the reaction mixture was allowed to warm to room temperature and then refluxed for 2.5 h during which the starting material was completely consumed. Heating was removed and the reaction mixture was allowed to cool down to room temperature. Ethanol was removed en vacuo and the reaction mixture was diluted with water (50 ml_) followed by extraction with Et2<D (50 ml_). The aqueous layer was acidified with 1 N HCI upto pH 3 and the precipitated product was filtered through a cintered funnel, washed with ice-cold water (10 ml_) and dried under high vacuum to give 2-(4-chlorophenoxy)acetic acid (20 g, 95.6% yield) as white solid. LCMS (ES) m/z = 186.1 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 4.65 (s, 2 H), 6.91 (d, J = 9.2 Hz, 2 H), 7.29 (d, J = 8.8 Hz, 2 H), 12.98 (bs, 1 H).
95.6%
With water; sodium hydroxide; In ethanol; at 0℃; for 2.58333h;Reflux;
To a solution of methyl 2-(4-chlorophenoxy)acetate (22.5 g, 1 12.15 mmol, 1 equiv) in ethanol (100 ml_) at 0 C was added a solution of sodium hydroxide (5.38 g, 134.58 mmol) in water (10 ml_). After stirring for 5 minutes at 0 C, the reaction mixture was allowed to warm to room temperature and then refluxed for 2.5 h during which the starting material was completely consumed. Heating was removed and the reaction mixture was allowed to cool down to room temperature. Ethanol was evaporated removed en vacuo and the reaction mixture was diluted with water (50 ml_) followed by extraction with Et20 (50 ml_). The aqueous layer was acidified with 1 N HCI up to pH 3 and the precipitated product was filtered through a cintered funnel, washed with ice-cold water (10 ml_) and dried under high vacuum to give 2-(4-chlorophenoxy)acetic acid (20 g, 95.6% yield) as white solid. LCMS (ES) m/z = 186.1 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 4.65 (s, 2 H), 6.91 (d, J = 9.2 Hz, 2 H), 7.29 (d, J = 8.8 Hz, 2 H), 12.98 (bs, 1 H).
95.6%
With water; sodium hydroxide; In ethanol; at 0℃;Reflux;
To a solution of methyl 2-(4-chlorophenoxy)acetate (22.5 g, 1 12.15 mmol, 1 equiv) in ethanol (100 mL) at 0 C was added a solution of sodium hydroxide (5.38 g, 134.58 mmol, 1 .2 equiv) in water (100 mL). After stirring for 5 minutes at 0 C, the reaction mixture was allowed to warm to room temperature and then refluxed for 2.5 h during which the starting material was completely consumed. Heating was removed and the reaction mixture was allowed to cool down to room temperature. Ethanol was removed en vacuo and the reaction mixture was diluted with water (50 mL) followed by extraction with Et20 (50 mL). The aqueous layer was acidified with 1 N HCI upto pH 3 and the precipitated product was filtered through a cintered funnel, washed with ice-cold water (10 mL) and dried under high vacuum to give 2-(4-chlorophenoxy)acetic acid (20 g, 95.6% yield) as white solid. LCMS (ES) m/z = 186.1 [M+H]+. 1 H NMR (400 MHz, DMSO-d6) delta ppm 4.65 (s, 2 H), 6.91 (d, J = 9.2 Hz, 2 H), 7.29 (d, J = 8.8 Hz, 2 H), 12.98 (bs, 1 H).
With lithium hydroxide monohydrate; In methanol; water; for 2h;Reflux;
General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH?H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.
With sulfuric acid; at 80℃; for 2h;
Add to the obtained methyl 4-chlorophenoxyacetate401.74g of 25% sulfuric acid, acid hydrolysis reaction at 80 C for 2h,At the same time, the alcohol formed by the reaction is distilled off, and the reaction is cooled to room temperature.Filter, add a small amount of water to wash the filter cake, filter cake to dry,186.82g of 4-chlorophenoxyacetic acid, the content of 98.6%,The total yield was 98.71% based on phenol.
186.44 g
To the obtained methyl 4-chlorophenoxyacetate, 401.74 g was added. 25% sulfuric acid, The acid hydrolysis reaction was carried out at 80 C for 2 h, and the alcohol formed by the reaction was distilled off. The reaction was cooled to room temperature, filtered, and the filter cake was washed with a small amount of water, and the filter cake was dried to obtain 186.44 g of 4-chlorophenoxyacetic acid, the content was 98.6. %, the total yield was 98.5% based on phenol.
182.27 g
With sulfuric acid; at 80℃; for 2h;
To the obtained methyl 4-chlorophenoxyacetate, 401.74 g of 25% sulfuric acid was added, and the acid hydrolysis reaction was carried out at 80 C for 2 h.At the same time, the alcohol formed by the reaction is distilled off, and the reaction is cooled to room temperature and filtered.The filter cake was washed with a small amount of water, and the filter cake was dried to obtain 182.27 g of 4-chlorophenoxyacetic acid.The content was 98.6%, and the total yield was 96.31% based on phenol.
With potassium carbonate; In N,N-dimethyl-formamide; at 90℃;
General procedure: To an oven-dried round bottomed flask with a stirring bar was added a solution of substituted phenol (0.01 mol, 1 eq.) and K2CO3 (1.2 eq.) in 50 mL of dry DMF. Excess ethyl chloroacetate dissolved in 10 mL of DMF was then slowly added through a dropping funnel to the above solution.The resulting mixture was stirred at 90 C for 5-6 h. The reaction was quenched with saturated NaCl solution, then extracted with dichloromethane(DCM), washed with brine, dried over MgSO4 and then concentrated on a rotary evaporator affording methyl 2-phenoxyacetate 1 (80%-95% yield) which was used for the next step without further purification [17].This product 1 (0.009 mol, 1 eq.) wasdissolved in 30 mL of ethanol and then placed in a round-bottomed flask equipped with a stirring bar; 80% of hydrazine hydrate (0.018 mol, 2 eq.) was slowly added to this mixture at room temperature through a dropping funnel. The resulting solution was heated up to reflux temperature and stirring was continued under this condition for another 6 h. The reaction mixture was filtered through celite,the filtrate was washed with brine, dried over MgSO4, and then concentrated in vacuo. The crudephenoxyacetohydrazide 2 was used directly without further purification in the next step.
With potassium carbonate; In 1-methyl-pyrrolidin-2-one;
Step A Preparation of 6-(4-chlorophenoxy)-8-methyl-2-(methylthio) pyrido[2,3-d]pyrimidin-7(8H)-one To a mixture of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde (0.55 g, 3.0 mmol) and <strong>[4841-22-9]methyl 4-chlorophenoxyacetate</strong> (prepared as in Example 4 using 4-chlorophenol, 0.66 g, 3.3 mmol) in 5 mL of 1-methyl-2-pyrrolidinone was added potassium carbonate (0.5 g, 3.6 mmol). The reaction mixture was heated to 120 C. and after 12 hours, additional phenoxyacetate (0.3 g, 1.5 mmol) and potassium carbonate (0.4 g, 2.9 mmol) was added. After 6 hours of stirring at 120 C., the reaction was cooled to room temperature and poured into water (100 mL). The reaction mixture was extracted with ethyl acetate (2*, 75 mL) and the resultant organic solution was washed with water (5*, 50 mL) then dried (brine, MgSO4). Evaporation of the solution yielded a solid which was recrystallized (EtOAc/Hexane) yielding 0.55 g of the sulfide (mass spec. M+1=334).
EXAMPLE 2 5-(p-Chlorophenoxy-acetamido)-4-methyluracil 60 g (0.3M) p-chlorophenoxyacetic acid methyl ester, 8.5 g (0.06M) 5-amino-4-methyluracil and 1.5 g ammonium chloride are heated four hours at 200 C. with stirring in a condenser. After cooling to about 50 C. 156 ml 96% ethanol is added and the suspension is stirred from 15 min. Subsequently the precipitate is filtered with suction, washed with ethanol and dried. The yield was 13.1 g (70.5% of theoretical) and the melting point was 280 to 293 C. (Decomp.). The raw product is recrystallized from 65 ml dimethylformamide with addition of 1.3 g of activated charcoal. The crystals are filtered with suction washed with dimethyl formamide and acetone and dried at 110 C. The yield was 5.3 g (28.5% of theoretical) and a melting point of 290-296 C. (decomp.). One obtains an additional 3.8 g (20.5% theoretical) by concentration of the mother liquor. The melting point of this additional material is 288 to 293 C. (decomp.). The total yield amounted to 9.1 g (49.% of theoretical).
hydrochloric acid salt of 1,3-bis(dimethylamino)-2-propyl-4-chlorophenoxyacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium ethanolate; In diethyl ether; benzene;
EXAMPLE 7 A mixture of 10.0 g (0.05 moles) of methyl-4-chlorophenoxyacetate, 7.35 g (0.05 moles) of 1,3-bis(dimethylamino)-2-propanol, 1.9 g of sodium ethylate and 30 ml. of benzene is heated to boiling for 10 hours and the methanol formed is continuously distilled off from the reaction mixture as an azeotropic mixture formed with benzene. The residual solution is distilled off in vacuo, the residue is dissolved in a 10:1 mixture of diethyl ether and acetone and the hydrochloric acid salt of 1,3-bis-(dimethylamino)-2-propyl-4-chlorophenoxyacetate is precipitated upon introducing gaseous hydrogen chloride.
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 ml_) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 ml_, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 C for 4 h. After consumption of the starting material (TLC, 5 % EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 ml_) and extracted with EtOAc (2 x 100 ml_). The combined organic layer was washed with brine solution (50 ml_), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15% ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4- chlorophenoxy)acetate (22.5 g, 96.5% yield) as pale yellow liquid. 1H NMR (400 MHz, CDC ): delta ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
96.5%
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 mL) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv ) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 mL, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 C for 4 h. After consumption of the starting material (TLC, 5 % EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15% ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5% yield) as pale yellow liquid. NMR (400 MHz, CDCI3): delta ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
96.5%
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h;
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 mL) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv ) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 mL, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 C for 4 h. After consumption of the starting material (TLC, 5 % EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15% ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4-chlorophenoxy)acetate (22.5 g,96.5% yield) as pale yellow liquid. LCMS (ES) m/z = 200.0 [M+H]+. 1 H NMR (400 MHz, CDCI3): delta ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
90%
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h;
General procedure: To a stirred solution of phenol (1 mmol) in DMF (3 mL) were added methyl bromoacetate (0.1 mL, 1 mmol) and K2CO3 (207 mg, 1.5 mmol), and the resulting mixture was heated at 80 C for 24 h. After cooling, the reaction mixture was diluted with EtOAc, and filtered by celite pad. The filtrate was evaporated, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 50 : 1 ~ 40 : 1) to give corresponding ether.
With 2,3,4-trichlorothiophene; thionyl chloride; lead acetate; at 20℃; for 0.5h;
To the methyl phenoxyacetate obtained by distillation, 0.09 g of lead acetate having a purity of 99% and 1.29 g of 2,3,4-trichlorothiophene having a purity of 99% were added.118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react, and the reaction was kept at this temperature for 0.5 h.Methyl 4-chlorophenoxyacetate was obtained in an amount of 203.77 g, and the content was 97.63%.
201.88 g
With 2,3,4-trichlorothiophene; thionyl chloride; lead(IV) tetraacetate; at 20℃; for 0.5h;
To the methyl phenoxyacetate obtained by distillation,Add 0.09g of lead acetate with a purity of 99% and 1.29g of 99% purity2,3,4-trichlorothiophene, 118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react, and the reaction was kept at this temperature for 0.5 h.The methyl 4-chlorophenoxyacetate was 201.88 g, and the content was 98.35%.
200.87 g
With 2,3,4-trichlorothiophene; thionyl chloride; lead acetate; at 20℃; for 0.5h;
To the obtained methyl phenoxyacetate,Add 0.09g of 99% pure lead acetate and 1.29g purity99% 2,3,4-trichlorothiophene,Add 118.34g purity at 20 C99% of thionyl chloride reacts,After the addition, the reaction was kept at this temperature for 0.5 h.Distilling at a pressure of 1 kPa and collecting fractions at 110-120 C,The methyl 4-chlorophenoxyacetate was obtained in an amount of 200.87 g, and the content was 98.84%.
200.87 g
With 2,3,4-trichlorothiophene; thionyl chloride; at 20℃; for 0.5h;
To the obtained methyl phenoxyacetate, Add 0.09g of lead acetate with a purity of 99% and 1.29g of 99% purity2,3,4-trichlorothiophene, 118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react.After the addition, the reaction was kept at this temperature for 0.5 h. Distilling at a pressure of 1 kPa and collecting fractions at 110-120 C, The methyl 4-chlorophenoxyacetate was obtained in an amount of 200.87 g, and the content was 98.84%.
200.87 g
With 2,3,4-trichlorothiophene; thionyl chloride; lead(IV) tetraacetate; at 20℃; for 0.5h;
To the methyl phenoxyacetate obtained by distillation,0.09 g of 99% pure lead acetate and 1.29 g of 99% pure 2,3,4-trichlorothiophene were added.118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react.After the addition, the reaction was kept at this temperature for 0.5 h.The fraction was distilled at a pressure of 1 kPa and collected at 110 to 120 C to obtain 200.87 g of methyl 4-chlorophenoxyacetate, and the content was 98.84%.
200.87 g
With 2,3,4-trichlorothiophene; thionyl chloride; lead(IV) tetraacetate; at 20℃; for 0.5h;
To the methyl phenoxyacetate obtained by distillation, 0.09 g of lead acetate having a purity of 99% and1.29g of 99% pure 2,3,4-trichlorothiophene, added 118.34g at 20 C99% pure thionyl chloride is reacted, and the reaction is kept at this temperature for 0.5 h, and distilled at a pressure of 1 kPa to collect a fraction of 110 to 120 C.The methyl 4-chlorophenoxyacetate was obtained in an amount of 200.87 g, and the content was 98.84%.
With sodium hydrogencarbonate; In water; at 80℃; for 2h;
To the obtained <strong>[4841-22-9]methyl 4-chlorophenoxyacetate</strong>, 87.07 g of 99% sodium hydrogencarbonate and 129.30 g of water were added, and the mixture was reacted at 80 C for 2 h.At the same time, the alcohol formed by the reaction is distilled off, and the reaction is cooled down to room temperature for filtration.The filter cake is dried to obtain 209.15 g of sodium 4-chlorophenoxyacetate, and the content is 98.6%.The total yield was 98.86% based on phenol.
With aluminum oxide; sodium; sodium hydroxide; In diethylene glycol; at 100℃; for 2h;
To the obtained <strong>[4841-22-9]methyl 4-chlorophenoxyacetate</strong>, 134.11 g of 99% pure isooctanol and 1.21 g of Na/NaOH/gamma-Al 2 O 3 (according to Gorzawski H., Hoelderich W. F.. Transesterification of methyl benzoate) were added.And dimethyl terephthalate with ethylene glycol over superbases [J]. Applied catalysis, 1999, 179: 131-137 prepared by the method), reacted at 100 C for 2 h, while distilling off the alcohol formed by the reaction,After completion of the reaction, filtration was carried out to obtain 299.03 g of isooctyl 4-chlorophenoxyacetate, the content was 98.6%, and the total yield was 98.66% based on phenol.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
