2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10060389, compound

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Reaction Steps

Compound 12 (3.00 g, 12.2 mmol) was dissolved in 25 mL of benzene and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.80 g, 12.2 mmol) was added slowly with stirring and stirring was continued for 3 h. The reaction mixture was filtered through a short column of alumina which was washed with dichloromethane. The solvent was evaporated from the colorless eluant and the residual product was crystallized from petroleum ether to give 2.83 g (11.6 mmol, 95%) of 18 as colorless microcrystalline plates: mp 62°-63° C.; 1H NMR: δ 1.51 (d, J=7.2 Hz, 6 H), 2.50 (s, 3 H), 3.88 (s, 3 H), 3.90 (sept, J=7.2 Hz, 1 H), 3.94 (s, 3 H), 7.01 (s, 1 H), 7.20 (d, J=8.3 Hz, 1 H), 7.60 (d, J=8.3 Hz, 1 H), 7.88 (s, 1 H). Anal. (C16H20O2) C, H.

Provenance & Evidence