반응 #55650

반응 방정식

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

ethanethiol

→

title compound

수율 88.0%

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

수율 88.0%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   기타results
2. 2
   온도the mixture is heated
3. 3
   workup.STIRRINGwith stirring in a bath at 165° C. for 6.0 hours
4. 4
   기타The mixture is then evaporated to dryness in vacuo
5. 5
   workup.DISSOLUTIONthe resulting residue is dissolved in water (50 ml)
6. 6
   추출extracted with ether (two 50 ml portions)
7. 7
   추출the ether extract
8. 8
   추출extracted with ethyl acetate
9. 9
   세척The ethyl acetate solution is washed with brine
10. 10
    건조dried with anhydrous magnesium sulfate
11. 11
    기타evaporated to a residue
12. 12
    기타Crystallization of this from chloroform-hexane

실험 절차

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.

출처