反应详情

To a stirred and refluxing Grignard-complex, previously prepared starting from 7.2 parts of magnesium and 81.4 parts of 2-(p-bromobenzyloxy)tetrahydropyran in 200 parts of dry tetrahydrofuran, is added dropwise a solution of 32.7 parts of 2-thiophenecarbonitrile in 70 parts of dry tetrahydrofuran (exothermic reaction: reflux temperature is maintained). Upon completion, stirring at reflux is continued for 4 hours. The reaction mixture is cooled and decomposed with 150 parts of a saturated ammonium chloride solution at about 15° C. The whole is poured onto water and the product is extracted with ether. The organic layer is washed four times with water, dried, filtered and acidified with gaseous hydrogen chloride; an oil is separated. The ether is decanted and the oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution. The solution is stirred with activated charcoal, filtered and the filtrate is stirred and refluxed for 10 minutes. The product is extracted with chloroform. The latter is washed with water, dried, filtered and evaporated. The residue is distilled, yielding α-hydroxy-p-tolyl 2-thienyl ketone; bp. 180°-190° C at 0.2 mm. pressure.

1. temperaturerefluxing Grignard-complex
2. custompreviously prepared
3. stirringUpon completion, stirring
4. temperatureat reflux
5. temperatureThe reaction mixture is cooled
6. additionThe whole is poured onto water
7. extractionthe product is extracted with ether
8. washThe organic layer is washed four times with water
9. customdried
10. filtrationfiltered
11. customan oil is separated
12. customThe ether is decanted
13. dissolutionthe oily product is dissolved in 300 parts of water and 150 parts of concentrated hydrochloric acid solution
14. stirringThe solution is stirred with activated charcoal
15. filtrationfiltered
16. stirringthe filtrate is stirred
17. temperaturerefluxed for 10 minutes
18. extractionThe product is extracted with chloroform
19. washThe latter is washed with water
20. customdried
21. filtrationfiltered
22. customevaporated
23. distillationThe residue is distilled