反応 #67719

反応方程式

water

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

1-bromo-2-chloro-ethane

sodium hydroxide

→

solid

収率 80.0%

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

収率 80.0%

反応条件

後処理

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

実験手順

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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