4-Hydroxybenzyl Alcohol → p-Hydroxymethylphenyl 4-vinylbenzyl ether

Participants

Reaction Steps

A mixture of 4-hydroxybenzyl alcohol (56.7 g, 0.459 molar), 85% potassium hydroxide (32.4 g, 0.459 molar) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (600 ml) was stirred at room temperature for 30 minutes. To this mixture was added 4-vinylbenzylchloride (70.5 g, 0.459 molar) very rapidly and it was then heated to 80° C. for 6 hours and stirred at ambient temperature overnight. The mixture was cooled, filtered and the solvent reduced to 300 ml by placing on a rotary evaporator. The solution was then placed in the freezer overnight. The next day the product was filtered to give a white solid. This material was recrystallized from methanol/dichloromethane (2/1) to give a white solid: m.p. of 110°-111.5° C. Yield of 77%. Analysis calculated for C16H16O2 : C, 79.97, H, 6.71. Found: C, 79.31, H, 6.69. 1H NMR (CDCl3) δ 2.55 (broad s, 1H, OH), 4.5 (s, 2H, CH2OH), 5.08 (s, 2H, ArCH2OAr), 5.25+5.75 (AB quartet, 2H, CH2 =), 6.8 (m, 1H, CH=), 6.8-7.6 (m, 8H, ArH's).

Provenance & Evidence