Reaction #1328421

Reaction equation

potassium carbonate

3-bromopropionic acid

methyl 2-mercapto-4-chlorobenzoate

→

Methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate

Solvents

acetone

Conditions

Workup

1. 1
   workup.DISTILLATIONThe solvent was distilled off
2. 2
   Extractionthe mixture was extracted with diethyl ether
3. 3
   Filtrationthe resulting precipitate was filtered off with suction
4. 4
   Otherdried

Procedure

179.5 g (1.3 mol) of potassium carbonate and, a little at a time, 94.5 g (0.62 mol) of 3-bromopropionic acid were added to a solution of 125.4 g (0.62 mol) of methyl 2-mercapto-4-chlorobenzoate in 1.5 l of acetone, and the reaction mixture was stirred at room temperature for 12 hours. The solvent was distilled off, the residue was taken up in water and the mixture was extracted with diethyl ether. The aqueous phase was then made acidic using concentrated hydrochloric acid, and the resulting precipitate was filtered off with suction and dried. This gave 150 g (88%) of methyl 2-(2-hydroxycarbonyleth-1-yl)thio-4-chlorobenzoate.

Source