反应 #67719

反应方程式

water

2-(benzo[d][1,3]dioxol-5-yl)acetonitrile

1-bromo-2-chloro-ethane

sodium hydroxide

→

solid

收率 80.0%

1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid

收率 80.0%

反应条件

后处理

1. 1
   温度heated at 130° C. for 48 hours
2. 2
   萃取extracted once with an equal volume of ethyl acetate and once with an equal volume of dichloromethane
3. 3
   过滤the precipitate filtered
4. 4
   洗涤washed with 1 M hydrochloric acid
5. 5
   workup.DISSOLUTIONThe solid material was dissolved in dichloromethane (400 mL)
6. 6
   萃取extracted twice with equal volumes of 1 M hydrochloric acid and once with a saturated aqueous solution of sodium chloride
7. 7
   干燥The organic solution was dried over sodium sulfate
8. 8
   其他evaporated to dryness

实验过程

A mixture of 2-(benzo[d][1,3]dioxol-5-yl)acetonitrile (5.10 g 31.7 mmol), 1-bromo-2-chloro-ethane (9.00 mL 109 mmol), and benzyltriethylammonium chloride (0.181 g, 0.795 mmol) was heated at 70° C. and then 50% (wt./wt.) aqueous sodium hydroxide (26 mL) was slowly added to the mixture. The reaction was stirred at 70° C. for 24 hours and then heated at 130° C. for 48 hours. The dark brown reaction mixture was diluted with water (400 mL) and extracted once with an equal volume of ethyl acetate and once with an equal volume of dichloromethane. The basic aqueous solution was acidified with concentrated hydrochloric acid to pH less than one and the precipitate filtered and washed with 1 M hydrochloric acid. The solid material was dissolved in dichloromethane (400 mL) and extracted twice with equal volumes of 1 M hydrochloric acid and once with a saturated aqueous solution of sodium chloride. The organic solution was dried over sodium sulfate and evaporated to dryness to give a white to slightly off-white solid (5.23 g, 80%) ESI-MS m/z calc. 206.1. found 207.1 (M+1)+. Retention time 2.37 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.07-1.11 (m, 2H), 1.38-1.42 (m, 2H), 5.98 (s, 2H), 6.79 (m, 2H), 6.88 (m, 1H), 12.26 (s, 1H).

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