Malonic Acid → 5-[3-(4,4-Dimethoxycyclohex-1-en-1-yl)propyl]oxolan-2-one

Participants

Reaction Steps

To a solution of 41 parts of tetrahydro-5-[3-(4-oxo-1-cyclohexen-1-yl)propyl]furan-2-one in 320 parts of methanol is added a solution of 20 parts of malonic acid in 160 parts of methanol. The resultant mixture is stirred at room temperatures for 7 hours, then cooled to 0°-5° and maintained thereat while being made basic with aqueous 5% sodium bicarbonate. The mixture thus obtained is extracted with ether. The ether extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is taken up in a 50:50 (by volume) mixture of ethyl acetate and hexane, and the resultant solution is filtered through silica gel. Solvent is removed from the filtrate by vacuum distillation, affording tetrahydro-5-[3-(4,4-dimethoxy-1-cyclohexen-1-yl)propyl]furan-2-one as the residue, an oil. It has the formula ##STR9##

Provenance & Evidence