3,4-Dihydroxybenzaldehyde → 3,4-dihexyloxybenzaldehyde

Participants

Reaction Steps

3,4-Dihydroxy-benzaldehyde (2.1 g, 0.015 mol), K2CO3 (4.0 g, 0.03 mol) and 1-iodohexane (6.4 g, 0.03 mol) were stirred in 100 ml of 1-butanol under reflux for 24 h. After cooling, the 1-butanol was removed by rotary evaporation. The residue was dissolved in 200 ml of ether, washed with water (dist.) and brine. The solution was dried over Na2SO4 and the solvent was removed to yield 3.7 g 3,4-Bis-hexyloxy-benzaldehyde (85%) as a dark solid. 1H NMR (400 MHz, CDCl3): δ 9.83 (s, 1H), 7.41 (m, 2H), 6.95 (d, 1H, J=8.5 Hz), 4.07 (m, 4H), 1.85 (m, 4H), 1.48 (m, 4H), 1.35 (m, 8H), 0.91 (m, 6H).

Provenance & Evidence