Acetyl chloride → 1-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Participants

Reaction Steps

A suspension of 3.45 g (25.9 mmol) aluminum chloride in 15 ml methylene chloride was cooled under argon in an ice-salt bath and treated with stirring with a mixture of 4 g (21.2 mmol) 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and 1.94 g (24.7 mmol) acetyl chloride via a dropping funnel over a period of thirty minutes. The cooling bath was removed and the mixture stirred for 2 hours, then quenched with ice. The organic layer was separated and the aqueous layer extracted with 2×50 ml methylene chloride. Organic extracts were combined and washed with water and saturated NaHCO3 solution and then dried (MgSO4). Solvent was removed in-vacuo and the residue distilled by the kugelrohr method (90° C.; 0.45 mm) to give the title compound as a colorless oil. PMR (CDCl3): δ 1.32 (6H, s), 1.33 (6H, s), 1.72 (4H, s), 2.60 (3H, s), 7.41 (1H, d, J~8.9 Hz), 7.71 (1H, dd, J~8.8, 2.6 Hz) 7.96 (1H, d, J~2.6 Hz).

Provenance & Evidence