Water → 2-(4-Methoxyphenyl)prop-2-enoic acid

Reaction equation

O[C:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.O>O1CCOCC1>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:2](=[CH2:6])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1

Participants

Procedure

2-Hydroxy-2-(4-methoxyphenyl)propionic acid (35 g, 178 mmol) was dissolved in dioxane (700 ml) and concentrated sulfuric acid (60 ml) was added thereto. The reaction mixture was refluxed for 2 hours under heating. The reaction solution was cooled and, after adding water, extracted with ethyl acetate. The organic layer was washed with saturated sodium thiosulfate solution and water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 24.8 g (yield: 72%) of the title compound as a brown solid.