tert-Butyl hydroperoxide → 4-Allyl-3-methoxy-4-methylnaphthalen-1(4h)-one

Participants

Reaction Steps

To a solution of Example 123B (7.72 g, 36.1 mmol) in benzene (400 mL) was added celite (15 g), pyridinium dichromate (54.3 g, 144.3 mmol) and tert-butylhydroperoxide (70% in water) (19.9 mL, 144.3 mmol). The resultant solution was stirred at room temperature for 1.25 hours, followed by filtering the solution through a plug of celite (20 g) which was rinsed with benzene (100 mL). The combined filtrate was concentrated in vacuo, and the resultant residue was purified by column chromatography employing 70-230 mesh silica gel eluting with a mixture of 20% ethyl acetate in hexane followed by 50% ethyl acetate in hexane to provide the title compound as a light yellow oil (2.05 g, 25%). 1H NMR (300 MHz, DMSO-d6): δ 1.53 (s, 3 H), 2.77 m, 2 H), 3.82 (s, 3 H), 4.75 m, 2 H), 5.02 (m, 1H), 5.84 (s, 1 H), 7.42 m, 1 H), 7.65 (dt, J=8.1, 1.5 Hz, 1 H), 7.76 (d, J=8.1 Hz, 1 H), 7.96 (dd, J=7.7, 1.5 Hz, 1 H).

Provenance & Evidence