p-Toluenesulfonic acid monohydrate → (S)-4-Benzyloxy-1,2-butanediol
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:15][O:14]C(C)(C)[O:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:12])[CH2:15][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In methanol (50 ml) were dissolved (S)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (2.06 g, 8.73 mmol) and p-toluenesulfonic acid hydrate (1.68 g, 8.8 mmol), and the solution was stirred at room temperature for 24 hours. After removal of methanol in vacuo, aqueous saturated sodium hydrogen carbonate was added to neutralize the solution. The solution was extracted with ethyl acetete and the extract was washed with saturated brine, dried on sodium sulfate, filtered, and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-4-benzyloxy-1,2-butanediol (1.70 g, yield 99%).