반응 #55646

반응 방정식

ethanethiol

3-(4-methoxyphenyl)glutaric acid

→

3-(4-hydroxyphenyl)-glutaric acid

수율 81.5%

용매

dimethylformamide

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   기타is removed by distillation in vacuo
2. 2
   workup.ADDITIONThe residue is diluted with water
3. 3
   추출extracted twice with ether (the extracts
4. 4
   추출extracted with ethyl acetate
5. 5
   세척The ethyl acetate solution is washed once with brine
6. 6
   기타dried
7. 7
   기타the residue crystallized from chloroform-hexane

실험 절차

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.

출처