반응 #46192

반응 방정식

AlCl3

methyl 1-(4-methoxyphenyl)cyclopropanecarboxylate

EtSH

→

1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester

수율 95.5%

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONwas added slowly at 0° C
2. 2
   기타the organic layer was separated
3. 3
   추출the aqueous phase was extracted with DCM (50 mL×3)
4. 4
   세척The combined organic layers were washed with H2O, brine
5. 5
   건조dried over Na2SO4
6. 6
   기타evaporated under vacuum

실험 절차

To a solution of methyl 1-(4-methoxyphenyl)cyclopropanecarboxylate (10.0 g, 48.5 mmol) in DCM (80 mL) was added EtSH (16 mL) under ice-water bath. The mixture was stirred at 0° C. for 20 min before AlCl3 (19.5 g, 0.15 mmol) was added slowly at 0° C. The mixture was stirred at 0° C. for 30 min. The reaction mixture was poured into ice-water, the organic layer was separated, and the aqueous phase was extracted with DCM (50 mL×3). The combined organic layers were washed with H2O, brine, dried over Na2SO4 and evaporated under vacuum to give 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (8.9 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.20-7.17 (m, 2H), 6.75-6.72 (m, 2H), 5.56 (s, 1H), 3.63 (s, 3H), 1.60-1.57 (m, 2H), 1.17-1.15 (m, 2H).

출처