P-Cresol → 1-methyl-4-(prop-2-yn-1-yloxy)benzene

Participants

Reaction Steps

To a solution of 10.8 g (0.1 mol) of p-cresol in 70 ml of absolute ethanol,there were added 4 g of sodium hydroxide. The reaction mixture was refluxeduntil complete dissolution and then treated with 16.36 g (0.1 mol) of propargyl bromide (80% in toluene). Reflux was resumed for 14 additional hours. The reaction mixture was then cooled, poured into water and extracted with hexane (3×100 ml). The combined organic extracts werewashed with 20% aqueous sodium hydroxide solution and water, dried over sodium sulfate and the solvent removed by evaporation. The residue was distilled at 102° C./15 mm to yield 3-(p-methylphenoxy)-1-propyne, identical to an authentic sample.

Provenance & Evidence