Toluene → HCID 11995324, compound

Participants

Reaction Steps

A mixture of 41.25 g. (200 mmoles) of ethyl 4-[(2-propenyl)oxy]phenylbenzoate, 15.0 g. (220 mmoles of sodium ethoxide and 13 ml. (240 mmoles) of acetonitrile in 85 ml. of dry toluene was mechanically stirred under a nitrogen atmosphere at 108° C. for 24 hours. The reaction mixture was cooled and diluted with 600 ml. of water. After all of the solid had dissolved, the mixture was washed with two 100 ml. portions of ethyl ether. The aqueous phase was then acidified to pH 5-6 with concentrated aqueous hydrochloric acid (required about 15 ml.). The precipitate which formed was collected by suction filtration, washed with water and air dried. This solid was sufficiently pure to carry directly into the next step. If desired, an analytically pure sample could be obtained by crystallization from an ethyl acetate/hexane mixture. 1H NMR (CDCl3, δ) 7.90 [d, 2H, J=9 Hz, phenyl-H(2]), 6.99 (d, 2H, J=9 Hz, phenyl-H(3)), 6.05 (m, 1H, vinyl CH), 5.43 (d, 1H, J=17 Hz, vinyl CH2), 5.35 (d, 1H, J=11 Hz, vinyl CH2), 4.63 (d, 2H, J=5 Hz, OCH2), 4,02 (s, 2H, CH2CN).

Provenance & Evidence