4-Hydroxybenzaldehyde → Ethyl 4-(4-formylphenoxy)butanoate

Participants

Reaction Steps

A solution of 4-hydroxybenzaldehyde (15.0 g, 0.122 mole) in butanone (200 ml) was treated with anhydrous potassium carbonate (18.55 g, 0.134 mole), and the mixture stirred at room temperature for 20 mins. Ethyl 4-bromobutanoate, (24.0 g, 0.122 mole), dissolved in butanone (10 ml), was added dropwise to the stirred mixture over a period of 1 h. The reaction was stirred and refluxed for 6 h, then cooled and partitioned between water and butanone. The organic phase was separated, washed with dilute sodium hydroxide, water, brine and dried, (MgSO4). Evaporation of the solvent in vacuo gave a red oil, which was distilled at 0.05 mm/Hg to yield 19.31 g (67%) of a colourless oil, bp 152°-6° C. υmax (film) 1730, 1685, 1600, 1580, 1508 cm-1 δ (CDCl3) 1.25 (3H, t, J 7 Hz, ester CH3) 2.18 (2H, bt, J6 Hz, OCH2CH2), 2.49 (2H, bt, J6 Hz, CH2CO2), 4.09 (2H, t, J6 Hz, OCH2), 4.11 (2H, q, J7 Hz, ester CH2), 7.38 (4H, ABq, Δυ75 Hz, J9 Hz, C6H4), 9.90 (1H, s, CHO)

Provenance & Evidence