Ethane → 3-Phenoxy-alpha-ethynylbenzylalcohol

Participants

Reaction Steps

Acetylene is dried through three traps, dry-ice-acetone, concentrated sulfuric acid and calcium chloride, and bubbled at about 5 psi pressure into dry THF (100 ml) for 10 minutes. Ethyl magnesium bromide (commercial, 0.14 mol) is added drop after drop over 2 hours at such a rate that the evolution of ethane is slowly and steady. After the addition, acetylene is bubbled through for 15 minutes. m-Phenoxybenzaldehyde (27.7 g, 0.14 mol) in THF (25 ml) is added to the reaction of 15° to 20° C. The reaction is allowed to raise to room temperature and stirred overnight. The complex is decomposed with saturated ammonium chloride solution. The product is extracted with ether, washed with water and dried (Na2SO4). Evaporation of the solvents, followed by vacuum distillation using Kugelrohn gives the alcohol (21.5 g).

Provenance & Evidence