반응 #2286278

반응 방정식

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

ethylene glycol dimethyl ether

potassium hydroxide

→

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

수율 5.5%

용매

water

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도to reflux for 2 d
3. 3
   농축The reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   추출extracted 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
   추출was extracted with ethyl acetate (2×100 mL)
8. 8
   세척washed with a saturated aqueous sodium chloride solution (2×50 mL)
9. 9
   건조dried with magnesium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated under vacuum
12. 12
    기타The solid was purified by column chromatography
13. 13
    세척eluted with 15-25% ethyl acetate in petroleum ether

실험 절차

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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