Methanol → Methyl 4-hydroxy-alpha-methylcinnamate

反応式

[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]=1

参加物

反応物 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 2191964-Hydroxy-alpha-methylcinnamic acid

生成物 1

HCID 53733305Methyl 4-hydroxy-alpha-methylcinnamate

実験手順

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.