|
In tetrahydrofuran; |
3-Benzyl-phenol (31) To a solution of m-hydroxybenzaldehyde 30 (5 g, 0.04 mol, 20 ml THF, 0 C.) was added phenylmagnesium bromide (32.8 ml, 3 M in THF, 0.010 mol). The reaction was stirred at 0 C. for one hour and then refluxed an additional hour. The solvent was removed by evaporation and the residue was dissolved in ether, extracted with 1 M HCl, washed with brine, and dried (MgSO4). 69 (crude): 1H NMR (500 MHz, CD3OD) delta9.25 (s, 1 H), 7.37-7.33 (m, 2H), 7.30-7.29 (m, 1 H), 7.20-7.18 (m, 1 H), 7.08-7.05 (m, 1H), 6.78-6.77 (m, 12 H), 6.58-6.55 (m, 1H), 5.78 (d, J=4.0 Hz), 5.59 (d, J=4.0 Hz). The crude benzyl alcohol, 30(a), was dissolved in methanol (20 ml) and hydrogenated (60 psi, 0.500 g Pd/C) for 5 hours. The reaction mixture was filtered through Celite and concentrated to yield the substituted phenol which was purified by column chromatography. (6.9 g, 0.038 mol, 93%). 1H NMR (500 MHz, CDCl3) delta7.30-7.27(m, 2 H), 7.21-7.13 (m, 4 H), 6.78-6.77 (m, 1 H), 6.67-6.65 (m, 1 H), 6.63 (s, 1 H), 3.93 (s, 2 H), 13C NMR (500 MHz, CDCl3) delta155.3, 142.8, 140.7, 129.5, 128.8, 128.3, 125.9, 121.3, 115.8, 113.0, 41.5. |