4-Hydroxybenzyl Alcohol → HCID 54467276, compound

Participants

Reaction Steps

Step 1) To a solution of para-hydroxybenzyl alcohol (2.0 g, 16.1 mol; Aldrich) dissolved in dry acetone (15 mL) was added K2CO3 (4.45 g, 32.2 mmol, 2.0 eq.) and ortho-nitrobenzylbromide (3.83 g, 17.7 mmol, 1.1 eq). The mixture was stirred at ambient temperature for 16 hr and then the solution was concentrated in vacuo. The residue was taken up in EtOAc (100 mL) and then the organic layer was washed with H2O (2×30 mL), brine (30 mL) and dried over MgSO4. The product was recrystallized from Et2O/hexanes to give yellow needles (2.0 g, 60%) of para-(ortho-nitrobenzyl)-hydroxybenzyl alcohol. 1H NMR (CDCl3, 400 MHz) d=8.16 (1H, dd, J=8.2, 1.3 Hz), 7.88 (1H, dd, 7.9, 1.0 Hz), 7.68 (1H, dt, J=7.5, 1.2 Hz), 7.51-7.46 (1H, m), 7.32-7.26 (2H, m), 6.98-6.95 (2H, m), 5.48 (2H, s), 4.61 (2H, s); 13C NMR (CDCl3, 100 MHz) d=157.6, 133.9, 128.7, 128.5, 128.2, 124.9, 114.8, 66.8, 64.9;

Provenance & Evidence