Protocatechuic Acid → Propargyl 3,4-Dihydroxybenzoate

Participants

Reaction Steps

Using the above procedure, 3,4-dihydroxybenzoic acid (0.0649 mole) and sodium hydroxide (0.0649 mole) were dissolved in 50% isopropyl alcohol (200 ml). Propargyl bromide (0.0649 mole) was added and the solution was heated to reflux for 6 hours. The solution was then cooled and the isopropyl alcohol was removed under vacuum. The residue was taken up in methylene chloride (200 ml), washed with water (200 ml), saturated sodium bicarbonate, saline and dried over magnesium sulfate. Removal of the solvent yielded crude product, which was recrystallized, from CCI4 to give the pure product. (68.0% yield) m.p. 127-129° C.

Provenance & Evidence