Diethyl Ether → 5,6,7,8-Tetrahydro-2-naphthoic acid

Participants

Reaction Conditions

Reaction Steps

1,2,3,4-Tetrahydro-6-naphthaldehyde (2.0 g) was suspended in 0.5M aqueous sodium hydroxide solution (125 ml), stirred vigorously and a 70% w/w solution of tertiary butyl hydroperoxide in water (10.3 ml) added. The mixture was heated at about 70° C. for 4 hours and then left to stand at room temperature for 3 days. A further quantity of a 70% w/w solution of tertiary butyl hydroperoxide in water (10 ml) was added and the mixture heated at about 70° C. for a further 24 hours. The mixture was cooled, diethyl ether (100 ml) added and the phases separated. The aqueous phase was acidified to pH 1 with 2N aqueous hydrochloric acid solution and extracted with diethyl ether (2×100 ml). The organic phases were combined, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with a solvent gradient of 1:1 changing to 1:0, by volume, diethyl ether:pentane to give 1,2,3,4-tetrahydro-6-naphthoic acid (0.62 g) as a white solid.

Provenance & Evidence