C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][SH:13])=[CH:10][CH:9]=1.Cl[CH2:17][C:18]([O:20][CH3:21])=[O:19].[I-].[K+]>CC(C)=O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][S:13][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:10][CH:9]=1Anhydrous acetone (100 ml), potassium carbonate (21 g), p-chlorobenzylmercaptan (19.5 ml), methyl chloroacetate (13.2 ml) and potassium iodide (0.1 g) are mixed in the cold. The mixture thus obtained is stirred and heated under reflux for 7 hours. It is cooled, the precipitate (K2CO3) is filtered off, the acetone is evaporated from the filtrate and the residue is taken up with ether. The ether solution is washed with 4 N NaOH and then with water until the wash waters have a neutral pH. The ether solution is then dried over MgSO4, the ether is evaporated and 34.5 g (100% yield) of methyl p-chlorobenzylmercapto-acetate are collected in the form of a chromatographically pure oil.
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