Acetic Acid → HCID 54327688, compound

Participants

Reaction Steps

A suspension of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3 -(2,4-dichlorophenoxy) propane (29.6 g) in diethyl oxalate (30 ml) was added to a suspension of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml). The resulting mixture was heated under reflux for 2 hours, cooled, and then poured onto ice (200 g). After acidifying with a solution of acetic acid (24 ml) in water (160 ml) the ethereal layer was separated. The aqueous layer was extracted with ether (3 × 50 ml) and the combined extracts evaporated to give a red oil. This was dissolved in ethanol (96%, 100 ml) containing hydrochloric acid (10 drops) and the solution heated under reflux for 1 hour. The solvent was then removed under reduced pressure to give a red oil which was solidified by triturating with ether. This solid was crystallized from ethanol to yield 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-(2,4-dichlorophenoxy) propane (30.5 g) as cream crystals m.p. 98°-100° C.

Provenance & Evidence