Methanol → 2-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-

反応式

[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH3:17]O>>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]([O:8][CH3:17])=[O:7]

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 983063-(2-Methylphenyl)prop-2-enoic acid

生成物 1

HCID 101763492-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-

反応条件

温度: 60 °C

実験手順

To 2-Methylcinnamic acid (5.68 g, 35 mmol) in MeOH (175 ml) was added thionyl chloride (2.55 ml, 35.0 mmol) dropwise. The resulting solution was stirred for 10 hours at 60° C. The solution was cooled to room temperature and concentrated. The crude ester was dissolved in CH2Cl2 and washed twice with saturated NaHCO3. The organics were combined, dried, and concentrated affording 6.45 g of methyl(2E)-3-(2-methylphenyl)acrylate.