反応 #46201

反応方程式

2-bromo-1,1-diethoxy-ethane

hydrogen

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

sodium hydride

→

1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid

収率 40.3%

溶媒

DMF

反応条件

後処理

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice (100 g)
2. 2
   抽出extracted with CH2Cl2
3. 3
   乾燥The combined organics were dried over Na2SO4
4. 4
   その他The solvent was evaporated under vacuum

実験手順

To a stirred solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (15.0 g, 84.3 mmol) in DMF (50 mL) was added sodium hydride (6.7 g, 170 mmol, 60% in mineral oil) at 0° C. After hydrogen evolution ceased, 2-bromo-1,1-diethoxy-ethane (16.5 g, 84.3 mmol) was added dropwise to the reaction mixture. The reaction was stirred at 160° C. for 15 hours. The reaction mixture was poured onto ice (100 g) and extracted with CH2Cl2. The combined organics were dried over Na2SO4. The solvent was evaporated under vacuum to give crude 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (10 g), which was used directly in the next step without purification.

出典