Potassium Carbonate → 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Participants

Reaction Steps

To a solution of acetic acid 2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester (4.03 g, 16.7 mmol) in methanol (50 mL) and dichloromethane (10 mL) is added potassium carbonate (2.33 g, 16.66 mmol). The reaction is permitted to stir for 8 hours at which time it is diluted with ethyl acetate and the resulting solution is washed successively with water and brine. The aqueous phases are then back-extracted with dichloromethane and the organic phases are then combined, dried over magnesium sulfate, filtered, and concentrated to furnish 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one; 1H NMR (400 MHz, CDCl3) δ ppm 1.04 (s, 3 H), 1.11 (s, 3 H), 2.07 (d, J=6.1 Hz, 1 H), 2.46 (d, J=16. 7 Hz, 1 H), 2.78 (d, J=16.7 Hz, 1 H), 4.64 (d, J=5.8 Hz, 1 H), 7.38-7.46 (m, 1 H), 7.59-7.63 (m, 2 H), 8.02 (d, J=7.8 Hz, 1 H).

Provenance & Evidence