反应详情

A suspension of 15 g. (0.023 M) of 2,2'-dihydroxybenzil dithallium salt in 500 ml. of dry toluene was stirred vigorously while adding dropwise a solution of 8.8 g. (0.05 M) of 3-dimethylamino-2-methyl propyl chloride in 91.5 ml. of toluene. The mixture was gradually heated to reflux during the addition, and the resulting mixture was stirred and refluxed for 12 hours before a color change was observed. After cooling to 25°, the pale yellow solid was filtered off and washed with toluene. The material was resuspended in toluene and filtered off again. The combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution, and finally dried over MgSO4. Evaporation of the dry toluene extract with heating up to 70° at 11 mm resulted in an oily residue. Various salts were prepared but failed to solidify. The free base was regenerated and the crude material began to crystallize. The product was recrystallized from hexane. After cooling to +5° overnight, the material was filtered off and dried in vacuo over P2O5 and paraffin wax to obtain 3.8 g. of the title compound; m.p. 69°-70°; λKbr/max 3.55, 5.88, 6.10, 6.55, 6.72 μ.

1. additionA suspension of 15 g
2. additionwhile adding dropwise a solution of 8.8 g
3. temperatureThe mixture was gradually heated
4. temperatureto reflux during the addition
5. temperaturerefluxed for 12 hours before a color change
6. temperatureAfter cooling to 25°
7. filtrationthe pale yellow solid was filtered off
8. washwashed with toluene
9. filtrationfiltered off again
10. washThe combined filtrates were washed with 10% sodium hydroxide solution, saturated brine solution
11. dry with materialfinally dried over MgSO4
12. customEvaporation of the dry toluene
13. extractionextract
14. temperaturewith heating up to 70° at 11 mm
15. customresulted in an oily residue
16. customVarious salts were prepared
17. customto crystallize
18. customThe product was recrystallized from hexane
19. temperatureAfter cooling to +5° overnight
20. filtrationthe material was filtered off
21. dry with materialdried in vacuo over P2O5 and paraffin wax
22. customto obtain 3.8 g