Methacrylic Acid → 2-Propynyl methacrylate

Participants

Reaction Steps

A solution of 86 g. (1 mole) of methacrylic acid in 120 ml. benzene was reacted with 67.2 g. (1.2 moles) of propargyl alcohol in the presence of 4 g. of p-toluenesulfonic acid as a catalyst and 0.4 g. p-tertbutylcatechol as an inhibitor. The reaction mixture was stirred and heated to reflux under nitrogen until 18 g. of water was azeotroped over into a Dean-Stark trap. The reaction mixture was neutralized with saturated sodium carbonate aqueous solution, washed with deionized water three times and dried over sodium carbonate. The solvent was removed on a Rotavapor. Vacuum distillation of the residue in the presence of the inhibitor gave a 75% yield of propargyl methacrylate obtained as a clear colorless liquid.

Provenance & Evidence