Reacción #2286285

Ecuación de reacción

(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

Rendimiento 98.3%

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

Rendimiento 98.3%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturato reflux for 24 h
3. 3
   ConcentraciónAt this time, the reaction mixture was concentrated under vacuum
4. 4
   workup.ADDITIONThe resulting solid was diluted with water (100 mL)
5. 5
   Extracciónextracted 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
   Extracciónwas extracted with ethyl acetate (2×50 mL)
8. 8
   Lavadowashed with a saturated aqueous sodium chloride solution (50 mL)
9. 9
   Secadodried with magnesium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated under vacuum
12. 12
    OtroThe resulting solid was dried under high vacuum overnight

Procedimiento

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

Fuente