p-Toluenesulfonic acid → 3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate

Participants

Reaction Steps

A round-bottomed flask was charged with 3-methyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenone (5) (3.8 g, 14.3 mmol), Isopropyl acetate (70 mL), and p-toluene sulfonic acid (1.4 g, 7.14 mmol). The reaction mixture was refluxed for 16 h under N2. Reaction mixture was cooled to room temperature and DDQ (9.74 g, 43 mmol) was introduced to the reaction mixture and refluxed for an additional 3 h. Reaction mixture was concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to afford 4.10 g (94%) of the title compound (6). 1H NMR (400 MHz, CDCl3): δ 7.64 (d, J=12.0 Hz, 1H), 7.55 (br s, 1H), 7.43 and 7.39 (dd, J1=16.0 Hz, J2=8.0 Hz, 2H), 7.38 and 7.34 (m, 1H), 7.26-7.24 (m, 2H), 7.14-7.11 (m, 2H), 3.92 (s, 3H), 2.22 (s, 3H), 2.00 (s, 3H).

Provenance & Evidence