Water → HCID 178526172, compound

Reaction equation

[CH:1](O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](O)(=O)[CH2:16][SH:17].[OH2:20]>FC(F)(F)C(O)=O>[CH:1]([CH2:15][C:16]([OH:20])=[S:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

To a solution of benzhydrol (100 g, 0.542 mol) in trifluoroacetic acid (300 mL) at room temperature (about 22 degrees C.) was added thioglycolic acid (50 g, 0.542 mol) drop wise over 20 minutes. Reaction progress was monitored by thin layer chromatography (TLC). The reaction was complete within one hour at which point water (1000 mL) was added slowly into the reaction mixture causing the product to precipitate. The resulting precipitate was filtered, washed with water and dried overnight under high vacuum to give benzhydrylthioacetic acid (139.3 g, 99.3%) as a pale yellow solid. (See Prisinzano, T. et al, Tetrahedron Asymm., 2004, 15, 1053-1058)