Octanoic Acid → Octanoic anhydride

Participants

Reaction Conditions

Reaction Steps

A glass reactor of 500 ml. capacity and equipped with a mechanical stirrer, temperature control means and a Dean-Stark type condenser was employed. To the reactor were charged 43.5 g. (300 millimols) of octanoic acid and 0.74 g. (3 m mols) of Co(OAc)2.4H2O. About 7 ml. of heptane was also added to the reactor and the Dean-Stark tube was filled with heptane. The reaction mixture was stirred vigorously and heated to 200° C. and nitrogen was bubbled through the reaction mixture at the rate of 50 cc/minute. The reaction was allowed to proceed for 3 hours under these conditions during which about 1 ml of H2O was collected in the Dean-Stark tube. Infrared analysis of the reaction mixture at the end of the 3 hour reaction period showed bands characteristic of the anhydride at 1825 and 1760 cm-1. GLC analysis of the reaction mixture showed that about 12% of the octanoic acid was converted to its anhydride to give 18 m mols of octanoic acid anhydride.

Provenance & Evidence