반응 #2286285

반응 방정식

(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

수율 98.3%

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

수율 98.3%

용매

water

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도to reflux for 24 h
3. 3
   농축At this time, the reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   추출extracted with ethyl acetate (2×50 mL)
6. 6
   workup.ADDITIONThe water layer was acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution
7. 7
   추출was extracted with ethyl acetate (2×50 mL)
8. 8
   세척washed with a saturated aqueous sodium chloride solution (50 mL)
9. 9
   건조dried with magnesium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated under vacuum
12. 12
    기타The resulting solid was dried under high vacuum overnight

실험 절차

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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