Cornforth reagent → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

Participants

Reaction Steps

To a stirred solution of 2.44 g (11.96 mmol) of 2-(1-hydroxyethyl)-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene in 35 ml of methylene chloride was added 6.75 g (17.9 mmol) of pyridinium dichromate and 330 mg (1.68 mmol) of pyridinium trifluoroacetate. The mixture was stirred at room temperature for 24 h and then diluted with 35 ml of low-boiling petroleum ether. The mixture was filtered through a short column of anhydrous MgSO4 and silica and the filtrate then concentrated in-vacuo to give the title compound as a colorless oil. PMR (CDCl3): δ 1.30 (6H, s), 1.60-1.70 (2H, m), 1.72-1.84 (2H, m), 2.56 (3H, s), 2.78 (2H, t, J~6.1 Hz), 7.08 (1H, d, J~7.8 Hz), 7.61 (1H, dd, J~7.8 Hz, 1.9 Hz), 7.93 (1H, d, J~1.9 Hz).

Provenance & Evidence