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

反応式

[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[OH-].[Na+].[CH2:11](Br)[C:12]#[CH:13]>O>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:13][C:12]#[CH:11])=[CH:1][CH:2]=1

参加物

実験手順

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.