4-Hydroxybenzoic Acid → Benzoic acid, 4-(2-propynyloxy)-, 2-propynyl ester

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Reaction Steps

A mixture of 8.0 g. of p-hydroxybenzoic acid, 125 ml. dimethylformamide, 13.0 g. of propargyl chloride and 24.0 g. of anhydrous potassium carbonate is heated at 75° for 32 hours and then is allowed to stand at room temperature for 3 days. Ether (150 ml.), pentane (100 ml.) and water (100 ml.) is added, the organic layer is separated and washed in turn with water (2 × 50 ml.) and saturated aqueous sodium chloride (1 × 50 ml.) and then is dried over calcium sulfate. Solvent is removed by rotary evaporation to yield propargyl 4-propargyloxybenzoate, m.p. 44.5-45.

Provenance & Evidence