Acetone → 10-Undecenoyl isocyanate

Participants

Reaction Steps

150 g of purified water was added to 45.5 g of sodium azide and a completely homogeneous solution was prepared by stirring while cooling with ice water. To this was added dropwise in small portions a solution prepared by mixing 101.4 g of 10-undecenoyl chloride with 150 mL of acetone; this addition was carried out so as to keep the solution temperature in the range from 10 to 15° C. Stirring at around 12° C. was continued for 1 hour after the completion of addition. The solution was then transferred to a separatory funnel and the aqueous and organic layers were separated. The organic layer was slowly added to 500 mL of toluene held at 60° C., followed by stirring for 3 hours in the temperature range from 50 to 60° C. The toluene was distilled off and distillation in vacuo was thereafter carried out to obtain 73.2 g of 10-undecenoyl isocyanate.

Provenance & Evidence