Ethanol → HCID 21544808, compound

Participants

Reaction Steps

A solution of 1-(2-acetyl-3-hydroxyphenoxy)-2-hydroxy-3-p-t-butylphenoxypropane (14.4 g) in diethyl oxalate (15 ml) was added to a suspension of sodium ethoxide, prepared from sodium (3.0 g) and ethanol (30 ml), in ether (200 ml). The mixture was heated under reflux for 1.5 hours, and the brown-coloured residue was 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 solution extracted with ether (3 × 25 ml). The solvent was then removed from the combined ethereal layer and ethereal extracts. The residue was dissolved in a mixture of acetic acid (80 ml) and hydrochloric acid (30 ml) and heated under reflux for 1 hour. On pouring into water (1 L) 1-(2-carboxychromon-5-yloxy)-3-p-t-butylphenoxypropane, 10.7 g, was obtained as a beige gum.

Provenance & Evidence