反応 #2286285

反応方程式

(3-chloro-4-hydroxy-5-methyl-phenyl)-acetonitrile

(3-Chloro-4-hydroxy-5-methyl-phenyl)-acetonitrile

ethylene glycol dimethyl ether

potassium hydroxide

→

(3-chloro-4-hydroxy-5-methyl-phenyl)-acetic acid

収率 98.3%

(3-Chloro-4-hydroxy-5-methyl-phenyl)-acetic acid

収率 98.3%

溶媒

water

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度to reflux for 24 h
3. 3
   濃縮At this time, the reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   抽出extracted with ethyl acetate (2×50 mL)
6. 6
   workup.ADDITIONThe water layer was acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution
7. 7
   抽出was extracted with ethyl acetate (2×50 mL)
8. 8
   洗浄washed with a saturated aqueous sodium chloride solution (50 mL)
9. 9
   乾燥dried with magnesium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated under vacuum
12. 12
    その他The resulting solid was dried under high vacuum overnight

実験手順

A suspension of (3-chloro-4-hydroxy-5-methyl-phenyl)-acetonitrile (4b) (1.3 g, 0.0071 mol) in water (2.06 mL) was treated with ethylene glycol dimethyl ether (13.93 mL, 0.133 mol) followed by potassium hydroxide (2.8 g, 0.0071 mol). The reaction mixture was heated to reflux for 24 h. At this time, the reaction mixture was concentrated under vacuum. The resulting solid was diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were discarded. The water layer was acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution (50 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting solid was dried under high vacuum overnight to afford (3-chloro-4-hydroxy-5-methyl-phenyl)-acetic acid (5b) (1.4 g, 97%) as a white solid; EI(+)-HRMS m/z calcd for C9H9ClO3 (M+) 200.0240, found 200.0247. Molecular Weight=200.6233; Exact Mass=200.0240

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