Acetone → 4-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one

Participants

Reaction Steps

To a solution of 19.5 g of the 2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-carboxaldehyde in 65 ml of acetone was added 32 ml of water and 36 g of 1% aqueous solution of sodium hydroxide. After refluxing for 20 hours, the reaction mixture was quenched with 2N hydrochloric acid and the aqueous layer was extracted three times with 50 ml of diethyl ether. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a crude product. Final purification was carried by recrystallization to afford 17.6 g of 4-(2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one as a yellow plate crystal.

Provenance & Evidence