Ethanol → Ethyl 3-(3-hydroxyphenyl)propanoate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])C(O)=O)[CH:5]=[CH:6][CH:7]=1.[OH2:13].[C:14]1([CH3:24])C=CC(S(O)(=O)=O)=CC=1.[CH2:25]([OH:27])C>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:12][C:25]([O:27][CH2:14][CH3:24])=[O:13])[CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
A solution of 3-Hydroxyphenylpropanoic acid (25 g, 150.60 mmol) and p-Toluenesulfonic acid monohydrate (3.80 g, 20 mmol) in abs ethanol (250 ml) was refluxed for 4 hours or until all the starting material is consumed. The reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound.