Hydroquinone → 2-Propenoic acid, (9Z)-9-octadecen-1-yl ester

Participants

Reaction Steps

To a 500 ml round bottom flask equipped with a stirrer, condenser, water trap and thermometer, was added oleyl alcohol (100 g, 0.373 moles), acrylic acid (27 g, 0.373) moles), p-toluenesulfonic acid monohydrate (1g, 1 wt%, hydroquinone (0.2 g, 0.2 wt%) and xylene (I00 ml). The reaction mixture was heated to reflux and maintained until no more water was collected (~4 hrs). The xylene solution was then concentrated to about half of its original volume. The crude product was then washed successively with water, saturated sodium bicarbonate solution, and then again with water. The organic solution was dried over sodium sulfate, filtered and the solvent evaporated under reduced pressure. The product was stabilized by 0.01 wt% of MEHQ. The yield was 80%.

Provenance & Evidence