反应 #55650

反应方程式

3-[2-(4-methoxyphenyl)ethyl]-glutaric acid

ethanethiol

→

title compound

收率 88.0%

3-[2-(4-Hydroxyphenyl)ethyl]glutaric acid

收率 88.0%

溶剂

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   其他results
2. 2
   温度the mixture is heated
3. 3
   workup.STIRRINGwith stirring in a bath at 165° C. for 6.0 hours
4. 4
   其他The mixture is then evaporated to dryness in vacuo
5. 5
   workup.DISSOLUTIONthe resulting residue is dissolved in water (50 ml)
6. 6
   萃取extracted with ether (two 50 ml portions)
7. 7
   萃取the ether extract
8. 8
   萃取extracted with ethyl acetate
9. 9
   洗涤The ethyl acetate solution is washed with brine
10. 10
    干燥dried with anhydrous magnesium sulfate
11. 11
    其他evaporated to a residue
12. 12
    其他Crystallization of this from chloroform-hexane

实验过程

To a suspension of 57% sodium hydride-paraffin (2.2 g) in dry dimethylformamide (70 ml) in an atmosphere of nitrogen is slowly added ethanethiol (4.0 ml). The mixture is stirred at room temperature until a clear solution results. To this solution is added a solution of 3-[2-(4-methoxyphenyl)ethyl]-glutaric acid (1.2 g) in dry dimethylformamide (10 ml) and the mixture is heated with stirring in a bath at 165° C. for 6.0 hours. The mixture is then evaporated to dryness in vacuo and the resulting residue is dissolved in water (50 ml), extracted with ether (two 50 ml portions) and the ether extract is discarded. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried with anhydrous magnesium sulfate, and evaporated to a residue. Crystallization of this from chloroform-hexane affords 1.0 g of the title compound, melting point 142°-144° C.

来源