Benzyl Chloride → Benzethonium Chloride

Participants

Reaction Steps

170.0 g of p-tert-octyl phenoxy ethoxy ethyl dimethylamine was added to a 1 L four-necked reaction flask, to which were sequentially added 100.2 g of methyl isobutyl ketone and 126.6 g of benzyl chloride. The reaction mixture was heated to reflux. The reaction was carried out for 2 hours. Then, 168.2 g of cyclohexane was added slowly. The flask was cooled to carry out crystallization. 156.8 g of a white solid was collected. The content of benzethonium chloride was 99.2% determined by titration according to the method described on page 247 of the United States Pharmacopeia USP29. The measured melting point was from 159.0 to 162.0° C. As calculated with reference to p-tert-octyl phenol, an overall yield of the three steps was less than 15%, which is remarkably far from that obtained by using a phase transfer catalyst. Thus, it does not have a practical application value.

Provenance & Evidence