Acetone → 3,5-Di(3,5-di(4-vinylbenzyloxy)benzyloxy)benzylalcohol

Participants

Reaction Steps

A 250 ml flask is charged with 15 g (34.5 mmol, 2.2 eq) of bromide (2) and acetone (100 ml) under an argon atmosphere. To this solution is added 3,5-dihydroxybenzyl alcohol (2.2 g, 15.7 mmol), 0.82 g (31.0 mmol, 0.2 eq) 18-C-6 and 4.77 g (34-5 mmol, 2.2 eq) of K2CO3 and the mixture is stirred for 48 hours whereupon a yellow suspension is formed. To the mixture is added methylene chloride (200 ml) and water (200 ml). The organic phase is separated, dried over MgSO4 and evaporated to dryness. A dark brown oil is obtained which is dissolved in toluene (40 ml) and hexane (20 ml). Upon cooling, a white powder forms which is collected by filtration to give 10.92 g (81.9% of (3A).

Provenance & Evidence