Acetic Acid → Tridec-4-en-1-yl acetate

Participants

Reaction Steps

495 g (2.2 moles) of the mixture of trans-4-tridecenyl chloride and cis-4-tridecenyl chloride synthesized in Example 1, 432 g (4.4 moles) of potassium acetate, and 264 g (4.4 moles) of acetic acid were mixed under an atmosphere of nitrogen (N2) and stirred at 180°-185° C. for 10 hours. Thereafter, this mixture was washed with 600 g of purified water and then with 600 g of a 5% aqueous solution of sodium bicarbonate. The resulting organic layer was purified by distillation. Thus, there was obtained 548 g (2.2 mole) of 4-tridecenyl acetate having a trans to cis ratio of 78:22 and a purity of 98%. This product is a sex pheromone component of the tomato pinworm (Keiferia lycopersicella) known as an insect pest of tomato fields principally in the United States of America.

Provenance & Evidence