* 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.
General procedure: A solution of 0.99 g (15.9 mmol) of dimethylsulfide in 3 mL of acetonitrile was added with stirring to a solution of 0.5 g (5.3 mmol) of 2-chloroacetic acid in 5 mL of the same solvent at room temperature. After the reaction completion, colorless crystals were filtered off, washed repeatedly with diethyl ether and dried in a vacuum.
156.5 g
at 40 - 50℃; for 20 h;
a) Preparation of β-Dimethylsulfonopropionic Acid Chloride (1)Add 4mol 3-chloropropionic acid and 6mol dimethyl sulfide in the reaction flask, stir and heat to 40-50 ° C to dissolve the 3-chloropropionic acid in dimethyl sulfide, add 700ml of organic solvent acetone During the operation, methyl ethyl ketone or ethyl acetate may be used instead of acetone as the organic solvent), and stirring is continued for 20 hours while maintaining the temperature at 50 ° C. The mixture is cooled in a water bath to cool down to 25 ° C and suction filtered. The filter cake was recrystallized from 1000 ml of 95percent (mass fraction) ethanol to obtain white crystal A, which was β-dimethylsulfonopropionate chloride, weighing 156.5 g.
Reference：
[1] Russian Journal of General Chemistry, 2017, vol. 87, # 9, p. 1903 - 1907[2] Zh. Obshch. Khim., 2017, vol. 87, # 9, p. 1419 - 1423,5
[3] Patent: CN107382802, 2017, A, . Location in patent: Paragraph 0011; 0013; 0015
2
[ 75-18-3 ]
[ 1259387-79-5 ]
[ 4337-33-1 ]
Yield
Reaction Conditions
Operation in experiment
72.3 g
Stage #1: at 20℃; for 4 h; Stage #2: With hydrogenchloride In water; toluene at 20℃; for 1 h;
Propionic acid (II) (84 g, 0.5 mol) and toluene (670 g) were added to the reactor, and the mixture was stirredAfter the mixture was stirred at room temperature for 4 hours, the reaction mixture was diluted with 5percent dilute hydrochloric acid (5 ml), and the mixture was stirred at room temperature for 1 hour. (I), methanesulfonic acid and hydrochloric acid solution, and then the mixed solution was adsorbed on the macroporous adsorption resin to remove the methanethiol Acid and hydrochloric acid to obtain an aqueous solution of dimethyl-β-propionate (I), which was evaporated to dryness to give the product dimethyl-β-propionate (I) as white powdery crystals 72. 3g, yield About 84.8percent.
1.2-3.2 (2) Synthesis of (2-carboxyethyl) dimethylsulfonium chloride:
Under stirring conditions, add 96g of the intermediate 3-(methylthio)propionic acid synthesized in step (1) to ethyl acetate, cool down to below 2°C in an ice bath, and then pass in 56g of methyl chloride and pass in 45 minutes. Continue to stir and react for 3.5 hours. After the reaction, the crude product of 2-(carboxyethyl)dimethylsulfonium bromide is obtained by suction filtration and drying at 50°C. The crude product is then recrystallized with anhydrous ethanol solution for 3 times. ) Drying to obtain 135.9 g of (2-carboxyethyl)dimethylsulfonium chloride.
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