Diethyl Ether → HCID 21544813, compound

Participants

Reaction Steps

To a suspension of sodium ethoxide, prepared from sodium (3.0 g) and ethanol (30 ml), in dry ether (200 ml), was added a solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-(2,5-dimethylphenoxy) propane (13.2 g) in diethyl oxalate (15 ml). The resultant solution was heated under reflux for 2 hours, and then poured onto ice (100 g). After acidification with a solution of acetic acid (12 ml) in water (80 ml), the ether layer was separated, and the aqueous layer extracted with ether (3 × 25 ml). The combined ethereal extracts were evaporated under reduced pressure to give a yellow oil. This was dissolved in ethanol (96%, 100 ml) containing hydrochloric acid (10 drops) and heated under reflux for 1 hour. Removal of the ethanol under reduced pressure gave 1-(2-carbethoxychromon-5-yloxy)-2-hydroxy-3-(2,5-dimethylphenoxy) propane as a yellow gum (15.2 g) which could not be crystallized.

Provenance & Evidence