Catechol → 2-(Hexyloxy)phenol

Participants

Reaction Steps

Catechol (35.0 g, 0.32 mol), potassium carbonate (109.0 g, 0.79 mol) and 1-bromohexane (52.5 g, 0.32 mol) were added to ethanol (300 ml) and heated under reflux for 48 h. After cooling, dichloromethane (300 ml) was added and the solid residues removed by filtration. The solvents were then removed in vacuo and the crude product was purified by column chromatography on silica gel to give title compound (17.9 g, 29%) as a colourless liquid. Found: C, 73.90; H, 9.20. C12H18O2 requires C, 74.19; H, 9.34. δH (CHCl3) 6.95-6.83 (m, 4H, ArH), 5.66 (s, 1H, OH), 4.04 (t, J 7, 2H, ArOCH2), 1.89-1.79 (m, 2H, ArOCH2CH), 1.55-1.35 (m, 6H, CH2), 0.95 (t, J 7, 3H, CH2CH3). MS (FAB), 194 (M+, 100%), 110 (45%), 95 (7%), 83 (12%), 69 (9%), 55 (18%).

Provenance & Evidence