[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CN(C)C=O.[CH2:16](Cl)[C:17]#[CH:18].C(=O)([O-])[O-].[K+].[K+].[CH3:26][CH2:27][CH2:28]CC>O.CCOCC>[CH2:16]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:28][C:27]#[CH:26])=[O:7])=[CH:4][CH:3]=1)[C:17]#[CH:18]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.
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