反应 #55646

反应方程式

ethanethiol

3-(4-methoxyphenyl)glutaric acid

→

3-(4-hydroxyphenyl)-glutaric acid

收率 81.5%

溶剂

dimethylformamide

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   其他is removed by distillation in vacuo
2. 2
   workup.ADDITIONThe residue is diluted with water
3. 3
   萃取extracted twice with ether (the extracts
4. 4
   萃取extracted with ethyl acetate
5. 5
   洗涤The ethyl acetate solution is washed once with brine
6. 6
   其他dried
7. 7
   其他the residue crystallized from chloroform-hexane

实验过程

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.

来源