Diethyl Ether → HCID 53656980, compound

Participants

Reaction Steps

To a suspensioin of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml) and dimethyl sulphoxide (50 ml), was added a suspension of 1-(3-acetyl-4 -hydroxyphenoxy- 2-hydroxy-3-(p-cyanophenoxy) propane (26.2 g) in diethyl oxalate (30 ml). The resulting suspension was heated under reflux for 2 hours, cooled, and poured onto ice (200 g). After acidification with a solution of acetic acid (24 ml) in water (160 ml), the ether layer was separated, and the aqueous layer extracted with ether (3 × 50 ml). The combined organic extracts were evaporated under reduced pressure to give a yellow solid. This was dissolved in ethanol (200 ml) containing hydrochloric acid (20 drops) and the solution heated under reflux for 1 hour. After cooling, the beige solid (20.0 g) was filtered off. Recrystallization from aqueous dioxane gave 1-(2-carbethoxychromon-6-yloxy)-2-hydroxy-3-(p-cyanophenoxy) propane (17.3 g) as pale yellow crystals, m.p. 150°-152° C.

Provenance & Evidence