反応 #2286278

反応方程式

(3,5-dimethyl-4-hydroxy-phenyl)-acetonitrile

ethylene glycol dimethyl ether

potassium hydroxide

→

(3,5-dimethyl-4-hydroxy-phenyl)-acetic acid

収率 5.5%

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 2 d
3. 3
   濃縮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 (2×75 mL)
6. 6
   workup.ADDITIONThe aqueous 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 (2×100 mL)
8. 8
   洗浄washed with a saturated aqueous sodium chloride solution (2×50 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 solid was purified by column chromatography
13. 13
    洗浄eluted with 15-25% ethyl acetate in petroleum ether

実験手順

A suspension of (3,5-dimethyl-4-hydroxy-phenyl)-acetonitrile (4a) (550 mg, 0.003 mol) in water (0.98 mL) was treated with ethylene glycol dimethyl ether (6.6 mL, 0.063 mol) followed by potassium hydroxide (1.34 g, 0.024 mol). The reaction mixture was heated to reflux for 2 d. The reaction mixture was concentrated under vacuum. The resulting solid was diluted with water (100 mL) and extracted with ethyl acetate (2×75 mL). The organic layers were discarded. The aqueous layer was acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution (2×50 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The solid was purified by column chromatography using silica gel eluted with 15-25% ethyl acetate in petroleum ether to afford (3,5-dimethyl-4-hydroxy-phenyl)-acetic acid (5a) (30 mg, 5%) as a yellow solid; EI(+)-HRMS m/z calcd for C10H12O3 (M+) 180.0786, found 180.0782. Molecular Weight=180.2053; Exact Mass=180.0786

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