Reacción #55649

Ecuación de reacción

3-[(4-methoxyphenyl)methyl]glutaric acid

ethanethiol

→

3-[(4-hydroxyphenyl)methyl]glutaric acid

Rendimiento 79.4%

Disolventes

dimethylformamide

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated in vacuo
2. 2
   Extracciónextracted with ether
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   Lavadowashed once with brine
5. 5
   Otrodried
6. 6
   Otroevaporated
7. 7
   Otrothe residue crystallized from a mixture of ethyl acetate-chloroform-hexane

Procedimiento

To a stirred suspension of 57% sodium hydride-paraffin (1.4 g) in dry dimethylformamide (30 ml) is added dropwise a solution of ethanethiol (4.0 ml) in dry dimethylformamide (10 ml). After 15 minutes, a solution of 3-[(4-methoxyphenyl)methyl]glutaric acid (800 mg) in dry dimethylformamide (20 ml) is added. The resulting slurry is heated in a bath at 165° C. for 20 hours and evaporated in vacuo. The residue is acidified with 20% hydrochloric acid, extracted with ether and the extracts are discarded. The aqueous solution is saturated with salt and extracted with ethyl acetate. The extracts are combined, washed once with brine, dried, evaporated and the residue crystallized from a mixture of ethyl acetate-chloroform-hexane to give 600 mg of 3-[(4-hydroxyphenyl)methyl]glutaric acid, melting point 117°-119° C.

Fuente