Dimethylhexadecylamine → HCID 70390925, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml flask commercial vinylbenzyl chloride (3.05 g, 0.020 mol) was mixed with hexadecyldimethylamine (5.4 g, 0.020 mol) without any additional solvent. After addition of 2,6-di-tert-butyl-4-methylphenol (100 mg, 0.45 mmol) the mixture was heated overnight at 50° C. The solid product which formed was washed several times with dry ether, dried under vacuum at room temperature, and recrystallized from acetone/ether to give 6.3 g (75%) of 4-styrylmethyl (hexadecyl)dimethylammonium chloride. 1H NMR (CDCl3 /Me4Si): 0.88 (s, 3H), 1.24 (br s, 26H ), 1.78 (s, 2H), 3.30 (s, 6H), 3.53 (s, 2H), 5.08 (s, 2H), 5.32 (d, J=10.8Hz, 1H), 5.84(d, J=18Hz, 1H), 6.7 (m, 1H), 7.51 (m, 4H). IR (KBr); 3020, 2920, 1640 cm-1. The critical micelle concentration (CMC) was 1.28× 10-2M at 25° C. determined conductometrically.

Provenance & Evidence