反应详情

温度

100 °C

The title compound was prepared following the method described in the literature (C. Jutz, W. Muller and E. Muller, Chem. Ber., 1966 99, 2479) for 3-formyl-4-phenylpyridine. ##STR10## Oxalyl chloride (34 ml; 0.39 moles) was added to a stirred solution of dimethylformamide (33 ml; 0.42 moles) in 1,2-dichloroethane (50 ml). To the resulting mixture was added α-methyl-p-fluorostyrene (13.6 g; 0.1 moles) in dichloroethane (20 ml) and the mixture refluxed for 3 hours. After removal of solvent by distillation under reduced pressure, water (150 ml) was added to give a dark brown solution. An aqueous solution of sodium perchlorate was added to this solution causing the di-iminium perchlorate (2) to precipitate. This was filtered off, washed with water, added to an aqueous solution of ammonium chloride (24 g in 190 ml of water) and heated at 100° C. for 1 hour. After allowing to cool, the reaction mixture was extracted with chloroform and the organic layer separated, washed with water, and ethereal HCl added causing the title compound (3) to precipitate as buff coloured crystals (18g; 76% yield based on styrene (1))

1. temperaturethe mixture refluxed for 3 hours
2. customAfter removal of solvent
3. distillationby distillation under reduced pressure, water (150 ml)
4. additionwas added
5. customto give a dark brown solution
6. customto precipitate
7. filtrationThis was filtered off
8. washwashed with water
9. additionadded to an aqueous solution of ammonium chloride (24 g in 190 ml of water)
10. temperatureto cool
11. extractionthe reaction mixture was extracted with chloroform
12. customthe organic layer separated
13. washwashed with water, and ethereal HCl
14. additionadded
15. customto precipitate as buff coloured crystals (18g; 76% yield based on styrene (1))