Oxalate → HCID 54479874, compound

Participants

Reaction Steps

To a suspension of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml) was added a solution of 1-(4-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-(p-cyanophenoxy) propane (26.2 g) and diethel oxalate (30 ml) in dimethyl sulphoxide (100 ml). After heating under reflux for 2 hours, the suspension was poured onto ice (200 g), acidified with a solution of acetic acid (24 ml) in water (160 ml), and the ether layer separated. The aqueous layer was extracted with ether (3 × 50 ml) and the combined ethereal extracts were evaporated under reduced pressure. The residue was dissolved in ethanol (200 ml) containing concentrated hydrochloric acid (20 drops) and the solution heated under reflux for 1 hour. Removal of the ethanol under reduced pressure gave a solid (24.6 g). On crystallization from ethanol 1-(2 -carbethoxychromon-7-yloxy)-2-hydroxy-3-(p-cyanophenoxy) propane was obtained as white crystals m.p. 170°-172° C.

Provenance & Evidence