5-Phenyl-1-pentanol → Benzenepentanal

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).

1. customseparated by 10 minute intervals
2. additionThe reaction mixture was treated with ethanol (20 ml)
3. customthen partitioned between water (500 ml) and ethyl acetate (500 ml)
4. extractionThe aqueous layer was extracted twice with ethyl acetate (500 ml)
5. washThe combined organic phases were washed with aqueous sodium thiosulphate (500 ml, 5%)
6. dry with materialwith water (200 ml), then with brine (200 ml), then dried over magnesium sulphate
7. customevaporated

ORD record

ord-90ac1b90566c4670ac0d425ee9a63bf3

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06306873B1