Carbon Dioxide → Octyl isocyanate

Participants

Reaction Steps

A Fischer-Porter bottle was charged with 0.65 g (5 mmol) of octyl amine, 2.74 g of BEMP (10 mmol), 25 mL of acetonitrile and 184 mg (1 mmol) of tridecane as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Fischer-Porter bottle was charged with 0.71 mL (5 mmol) of trifluoroacetic anhydride and 25 mL of acetonitrile then pressurized to 80 psig with CO2. The two solutions were cooled to 0° C. in an ice bath for 10 minutes after which time the octyl carbamate solution was added rapidly to the trifluoroacetic anhydride solution. An aliquot was taken after five minutes and diluted with diethyl ether prior to G.C. analysis which indicated a yield of 83% octyl isocyanate. The reaction mixture was allowed to warm slowly to room temperature and aliquots were taken periodically for G.C. analysis. A maximum yield of 85% octyl isocyanate was obtained after ca. 30 minutes.

Provenance & Evidence