반응 #69653

반응 방정식

Ethyl 4-hydroxybenzoate

potassium carbonate

3-methyl-2-butenyl chloride

→

ethyl 4-(3-methyl-but-2-enyloxy)-benzoate

수율 95.2%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도at reflux for 3 hours
2. 2
   온도Upon cooling the solvent
3. 3
   기타was removed in vacuo
4. 4
   기타the mixture partitioned between dichloromethane and water
5. 5
   기타The organics were separated
6. 6
   기타the solvent removed in vacuo

실험 절차

Ethyl 4-hydroxybenzoate (1.66 g, 10.0 mmol) and anhydrous potassium carbonate (2.07 g, 15.0 mmol) in acetonitrile (30 ml) was treated with 3-methyl-2-butenyl chloride (1.35 ml, 12.0 mmol) and the mixture was stirred and held at reflux for 3 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between dichloromethane and water. The organics were separated and the solvent removed in vacuo to afford ethyl 4-(3-methyl-but-2-enyloxy)-benzoate (2.23 g, 95%) as a pale yellow liquid which was used without further purification. 1H NMR (DMSO-d6) 7.89 (2H, d), 7.04 (2H, d), 5.44 (1H, t), 4.62 (2H, d), 4.28 (2H, q), 1.77 (3H, s), 1.73 (3H, s), 1.31 (3H, t). MS: [M+H]+ 235.

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