2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate

3-Ethyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenone (55) (0.84 g, 3.00 mmol) was dissolved in isopropenyl acetate (30 mL). pTsOH monohydrate (100 mg) was added. The mixture was refluxed under nitrogen for 3 days. Cooled to room temperature, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.74 g, 7.50 mmol) was added. The resulting mixture was refluxed under nitrogen overnight. Cooled to room temperature and diluted with CH2Cl2 (150 mL). The mixture was washed with 0.2 N NaOH (4×20 mL), water (2×20 mL), brine (30 mL), dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a dark brown tar. The crude product was purified by flash chromatography over SiO2 with hexanes:acetone (50:1) to give 0.61 g (64%) of the title compound (56) as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.11 (t, J=7.5 Hz, 3H), 1.97 (s, 3H), 2.55 (q, J=7.5 Hz, 2H), 3.93 (s, 3H), 7.10-7.16 (m, 2H), 7.20-7.25 (m, 2H), 7.30-7.45 (m, 3H), 7.57 (s, 1H), 7.62 (d, J=8.9 Hz, 1H).

1. temperatureThe mixture was refluxed under nitrogen for 3 days
2. temperatureThe resulting mixture was refluxed under nitrogen overnight
3. temperatureCooled to room temperature
4. washThe mixture was washed with 0.2 N NaOH (4×20 mL), water (2×20 mL), brine (30 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customto give the crude product as a dark brown tar
9. customThe crude product was purified by flash chromatography over SiO2 with hexanes:acetone (50:1)

ORD record

ord-726360292c9d4e7cb423249c60297b37

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649093B2