Phenol → 3-methoxy-4-(2-propenyloxy) benzenemethanol

Participants

Reaction Conditions

Reaction Steps

Acetone (107.5 mL), vanillyl alcohol (25 g, 0.163 mol), and allyl bromide (15.8 mL, 0.183 mol) were added to a 250 mL, round-bottomed flask and stirred until homogeneous. Potassium carbonate (22.5 g, 0.163 mol) was then added slowly, which briefly gave a light pink color that indicated deprotonation of the phenol. The mixture was heated at 60° C. overnight. The reaction was monitored by TLC using 10% acetone in CH2Cl2 as eluent. Upon completion, the reaction mixture was allowed to cool to rt with stirring. The acetone was removed under vacuum, yielding a white residue. CH2Cl2 (200 mL) and H2O (200 mL) were added to redissolve the residue and transferred to a separatory funnel. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (3×100 mL) and saturated NaCl (1×100 mL). The organic layer was then collected, dried over MgSO4. After filtration, the solvent was removed under vacuum to afford a yellow powder. The yellow powder was redissolved in EtOAc (250 mL), which was subsequently removed under vacuum (in order to remove excess allyl bromide) to afford the product as a fine, white powder (30.0 g, 93% yield). 1H NMR δ=6.94 (s, 1H), 6.86 (s, 2H), 6.09 (multi, 1H), 5.42 (dd, J1=20, J2=1.5, 1H), 5.30 (dd, J1=20, J2=1.5, 1H), 4.63 (d, J=3.6, 2H), 4.62 (d, J=5, 2H), 3.89 (s, 3H), 1.57 (t, J=6, 1H).

Provenance & Evidence