Methanol → Methyl 4-hydroxy-alpha-methylcinnamate
Reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]([CH3:11])[C:8]([O:10][CH3:19])=[O:9])=[CH:12][CH:13]=1Participants
4
Procedure
To 4-hydroxy-α-methylcinnamic acid (55 g), absolute methanol (400 ml) and conc. sulfuric acid (10 ml) were added and refluxed for 12 hours. After the reaction mixture was allowed to cool, it was concentrated under reduced pressure. To the residue was added water (300 ml), and the mixture was neutralized with sodium hydrogen carbonate, and the resulting precipitate was collected by filtration, washed with water, and recrystallized from ethyl acetate/nhexane to give methyl 4-hydroxy-α-methylcinnamate (53 g). mp. 103°-104° C.