反应详情

To vigorously stirred 2-phenylbenzonitrile (68.1 g) under ice-cooling was added titanium tetrachloride (432 g) dropwise for 30 minutes. The precipitated crystals were pulverized and then chloromethyl-methyl ether (61 g) was added dropwise for 20 minutes with stirring under ice-cooling. After stirring at 60° C. for 2 hours, additional chloromethyl-methyl ether (15.3 g) was added and the mixture was stirred for an additional hour. To the reaction mixture was added ethyl acetate (200 ml) dropwise with stirring under ice-cooling. Then ice was added until hydrogen chloride gas development ceased and iced water (400 ml) was added before stirring for a while. The precipitated crystals were filtered and dried. The filtrate was extracted with ethyl acetate, washed with water, and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography on silica gel to give crystals which were combined with the previously obtained crystal and recrystallized from methanol to yield pale yellow prisms (41.8 g, 48%).

1. temperaturecooling
2. stirringAfter stirring at 60° C. for 2 hours
3. stirringthe mixture was stirred for an additional hour
4. stirringwith stirring under ice-
5. temperaturecooling
6. stirringbefore stirring for a while
7. filtrationThe precipitated crystals were filtered
8. customdried
9. extractionThe filtrate was extracted with ethyl acetate
10. washwashed with water
11. concentrationconcentrated to dryness in vacuo
12. customThe resulting residue was purified by column chromatography on silica gel
13. customto give crystals which
14. customrecrystallized from methanol