4-Hydroxybenzyl Alcohol → (4-(Prop-2-en-1-yloxy)phenyl)methanol

Participants

Reaction Steps

A mixture of 4-hydroxybenzylalcohol (1.52 g, 12.2 mmol.), allyl bromide (1.1 ml, 12.2 mmol.), acetonitrile (40 ml), and potassium carbonate (2.54 g, 18.4 mmol.) was reluxed for 18 hours, then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4) and evaporated to give the product as a yellow oil (0.72 g, 71%). 1H NMR (300 MHz, CDCl3) δ 2.1 (s, 1H), 4.55 (m, 2H), 4.6 (s, 2H), 5.3 (d, 1H, J=11.5 Hz), 5.43 (d, 1H, J=16.5 Hz), 6.1 (m, 1H), 6.94 (m, 2H), 7.33 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 65.3, 69.2, 115.2, 118.1, 129.0, 129.4, 133.7, 158.6.

Provenance & Evidence