Reaktion #2286278

Reaktionsgleichung

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

ethylene glycol dimethyl ether

potassium hydroxide

→

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

Ausbeute 5.5%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturto reflux for 2 d
3. 3
   EinengenThe reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   Extraktionextracted with ethyl acetate (2×75 mL)
6. 6
   workup.ADDITIONThe aqueous layer was acidified to pH=2 by the addition of a 1N aqueous hydrochloric acid solution
7. 7
   Extraktionwas extracted with ethyl acetate (2×100 mL)
8. 8
   Waschenwashed with a saturated aqueous sodium chloride solution (2×50 mL)
9. 9
   Trocknendried with magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated under vacuum
12. 12
    SonstigeThe solid was purified by column chromatography
13. 13
    Wascheneluted with 15-25% ethyl acetate in petroleum ether

Vorschrift

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

Quelle