Abstract
4-Chloro-2, 5-dimethylstyrene (3a) was easily obtained by dehydration of 4-chloro-2, 5-dimethylphenylmethylcarbinol (2a) prepared by the action of 4-chloro-2, 5- dimethylphenylmagnesium chloride on acetaldehyde.
Instead of acetaldehyde, the reaction was carried out with acetone, in which case the product was 4-chloro-2, 5-dimethyl-α-methylstyrene (3b).
2, 5-Dimethyl-4-vinylbenzoic acid (4), 2, 5-dimethyl-4- (N, N-dimethylaminomethyl) styrene (6a), 4- (N, N-diethylaminomethyl) -2, 5-dimethylstyrene (6b) and 2, 5-dimethyl-4- (N, N-di-n-propylaminomethyl) styrene (6c) were synthesized by the addition of the Grignard reagent prepared from (3a) to carbon dioxide, N, N-dimethylaminomethyl-iso-butyl ether, N, N-diethylaminomethyl-n-butyl ether and N, N-di-n-propylaminomethyl-n-butyl ether, respectively.
(4), (6a), (6b) and (6c) could be polymerized in the presence of 2, 2'-azobisisobutyronitrile.
When the Grignard reagent prepared from (3b) was used, the resulting products were 2, 5-dimethyl 4 (N, N-dimethylaminomethyl) -α-methylstyrene (8a), 4- (N, N-diethylaminomethyl) -2, 5-dimethyl-α-methylstyrene (8b) and 2, 5-dimethyl-4- (N, N-di-n-propylaminomethyl) -α-methylstyrene (8c).
