Dimethyl Sulfoxide → 11-Hexadecenal, (11Z)-

Participants

Reaction Conditions

Reaction Steps

Run 3 (invention): The oxidation procedure employed for run 2 was repeated on a larger scale. Thus, 360 g (1.2 mol) of hexadecenyl bromide and 1800 mL (1980 g; 25.4 mol) of DMSO were mixed and heated to 60° C., with temperature maintained at 60° C. for about 30 minutes. Then, 240 g (2.9 mol) of NaHCO3 was added and the temperature of the reaction mixture raised to 130° C., which was maintained for 2 hours. The reaction mixture was then cooled and filtered. The lower layer (DMSO layer) was separated and extracted with about 1 L of hexane. The hexane extract and upper (aldehyde) layer were combined, washed once with about 100 mL of water, then concentrated on a rotary evaporator. GLC analysis indicated an aldehyde/alcohol ratio of 4.5:1. A distilled yield of 38% Z-11-hexadecenal was obtained.

Provenance & Evidence