Reacción #55646

Ecuación de reacción

ethanethiol

3-(4-methoxyphenyl)glutaric acid

→

3-(4-hydroxyphenyl)-glutaric acid

Rendimiento 81.5%

Disolventes

dimethylformamide

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrois removed by distillation in vacuo
2. 2
   workup.ADDITIONThe residue is diluted with water
3. 3
   Extracciónextracted twice with ether (the extracts
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe ethyl acetate solution is washed once with brine
6. 6
   Otrodried
7. 7
   Otrothe residue crystallized from chloroform-hexane

Procedimiento

To a stirred suspension of 57% sodium hydride-paraffin (6.45 g), in dry dimethylformamide (70 ml) is slowly added ethanethiol (11.89 ml) in dry dimethylformamide (20 ml). After stirring the resultant slurry for 15 minutes, a solution of 3-(4-methoxyphenyl)glutaric acid (3.0 g) in dry dimethylformamide (20 ml) is added. The slurry is heated in a bath at 165° C. for 5.0 hours and most of the solvent is removed by distillation in vacuo. The residue is diluted with water, acidified with concentrated hydrochloric acid and extracted twice with ether (the extracts are discarded). The solution is saturated with sodium chloride and extracted with ethyl acetate. The ethyl acetate solution is washed once with brine, dried and the residue crystallized from chloroform-hexane to afford 2.3 g of 3-(4-hydroxyphenyl)-glutaric acid, melting point 168°-170° C.

Fuente