5-Phenyl-1-pentanol → Benzenepentanal

Participants

Reaction Steps

A vigorously stirred solution of 5-phenylpentanol (10 g), sodium bromide (6.45 g) and TEMPO, 2,2,6,6-tetramethyl-1-piperidinyloxy, (0.095 g) in a mixture of ethyl acetate, toluene and water (258 ml, 7:7:1, v/v/v), at 0° C., was treated with aqueous sodium hypochlorite solution (571 ml, 0.35M) saturated with sodium bicarbonate (43.85 g) in five portions separated by 10 minute intervals. The reaction mixture was treated with ethanol (20 ml) then partitioned between water (500 ml) and ethyl acetate (500 ml). The aqueous layer was extracted twice with ethyl acetate (500 ml). The combined organic phases were washed with aqueous sodium thiosulphate (500 ml, 5%), then with water (200 ml), then with brine (200 ml), then dried over magnesium sulphate and then evaporated to give the title compound as an orange oil, which was used without further purification. NMR (CDCl3): δ1.65 (m,4H), 2.35 (m,2H), 2.60 (t,2H), 7.10-7.30 (m,5H), 9.75 (s,1H).

Provenance & Evidence