Reaktion #2286285

Reaktionsgleichung

(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

Ausbeute 98.3%

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

Ausbeute 98.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturto reflux for 24 h
3. 3
   EinengenAt this time, the reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   Extraktionextracted 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
   Extraktionwas extracted with ethyl acetate (2×50 mL)
8. 8
   Waschenwashed with a saturated aqueous sodium chloride solution (50 mL)
9. 9
   Trocknendried with magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated under vacuum
12. 12
    SonstigeThe resulting solid was dried under high vacuum overnight

Vorschrift

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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