4-Methoxybenzyl alcohol → 4-((4-Methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acid

Participants

Reaction Steps

A 250 ml one-necked round bottomed flask equipped with reflux condenser, nitrogen inlet, and magnetic stir bar was charged with itaconic anhydride (33.6 g, 0.3 mol) toluene (100 ml) and 4-methoxybenzyl alcohol (41.5 g, 0.3 mol). The solution was then warmed to reflux for 60 minutes and then cooled to room temperature. The solution was poured into a 500 ml Erlenmeyer flask, diluted with 100 ml of hexane and allowed to stand whereupon crystals of pure monoester formed. The product was isolated by filtration on a Buchner funnel and air dried to give 45.4 g, 61% of material with mp 83°-85° C., a second crop, 12.9 g, 17% was isolated after cooling of the filtrate in an ice bath.

Provenance & Evidence