B(F)(F)F.CCOCC.[CH2:10]([S:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[C:21](O)=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.[BH4-].[Na+].Cl.O>[CH2:10]([S:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[C:27]([O:29][CH3:30])=[O:28])[CH2:21][OH:22])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
28 ml of boron trifluoride etherate is added to a suspension of 46 g of crude 3-benzylmercapto-4-carbomethoxy benzoic acid in 750 ml of anhydrous tetrahydrofuran and 7 g of sodium borohydride. The reaction mixture is stirred for 3-4 hours at room temperature, then diluted with about 20 ml of 2N hydrochloric acid and 500 ml of water. The product obtained is extracted with ether and the ether extract is washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. Crystallization from ethyl acetate:hexane (1:2) yielded 28.6 g of 3-benzylmercapto-4-carbomethoxy benzyl alcohol having a melting point of 89.5°-92° C.
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