Methanol → methyl (E)-beta-methoxy-2-methylcinnamate

反応式

[CH:1]([O:6]C)([O:4][CH3:5])OC.[CH3:8][OH:9].OS(O)(=O)=O.N1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:8][O:9]/[C:17](/[C:18]1[CH:19]=[CH:18][CH:17]=[CH:16][C:19]=1[CH3:20])=[CH:16]/[C:1]([O:4][CH3:5])=[O:6]

参加物

反応物 4

HCID 887Methanol

HCID 1049Pyridine

HCID 1118Sulfuric Acid

HCID 9005Trimethyl orthoformate

生成物 1

HCID 86749647methyl (E)-beta-methoxy-2-methylcinnamate収率 94%

実験手順

A mixture of 1280 g (6.7 mol) of methyl 2-methylbenzoyl acetate, 848 g (8.0 mol) of trimethyl orthoformate, 400 ml of methanol and 10 ml of concentrated H2SO4 is stirred at room temperature for 12 h. The mixture is subsequently neutralized with 20 ml of pyridine and then concentrated, and the residue is fractionally distilled (boiling point 120°-123° C./0.6 torr). 1300 g (94%) of methyl (E)-β-methoxy-2-methylcinnamate are obtained as a pale yellow oil.