Acetyl chloride → 1-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one

Participants

Reaction Steps

To a suspension of AlCl3 (6.6 g, 49.6 mmol) in CH2Cl2 (225 mL) at 0° C. was added acetyl chloride (3.5 mL, 49.6 mmol) dropwise via syringe. To the resulting homogeneous light brown solution was added 6-methoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene (Intermediate 2, 9.0 g, 41.3 mmol) in CH2Cl2 (25 mL) via cannula. The mixture was then stirred at ambient temperature for 1 h, poured onto ice and extracted with Et2O (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound as a white solid (10.7 g, 100%).

Provenance & Evidence