4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

Participants

Reaction Steps

A solution of potassium hydroxide (13.2 g) and 4-hydroxybenzaldehyde (20.6 g, 169 mmol) in ethanol (320 ml) was refluxed for 30 min. 6-Bromohexanol (24.5 g, 135 mmol) dissolved in ethanol (30 ml) were added and the reaction mixture was refluxed for 16 h. The solvent was then removed in vacuo. Dichloromethane (400 ml) was added no the residue. The organic layer was washed with aqueous sodium hydroxide (1 M, 300 ml), water (500 ml) and brine (250 ml), filtered, dried over anhydrous sodium sulfate and concentrated in vacuo. Recritstallisation of the residue from dichloromethane/petroleum ether yielded (13) as a pale yellow solid (16.7 g, 45%). The analytical data was in accordance with that reported by C. Noel, C. Friedrich, V. Leonard, P. LeBarney, G. Ravaux, and J. C. Dubois, Makromol. Chem., Macromol. Symp., 1989, 24, 283.

Provenance & Evidence