2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13075704, compound

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Reaction Steps

A mixture of (2) (893 mg) and DDQ (2.2 g) in dioxane (50 ml) was stirred for 15 hr at 80°-90° C. and then refluxed for 4 hr. After cooling to room temperature the precipitate was filtered off and the filtrate was diluted with ether which was successively washed with 1 N-KOH and brine. The extract was purified by silica gel column (AcOEt-n-hexane, 1:20 to give 490 mg (55%) of the trienone (3); mp 166°-168° C. (from AcOEt-cyclohexane), MS m/e 504(M+), 489; IR(KBr), 3180, 1650, 1595 cm-1 ; NMR(CDCl3)δ0.72(s, 18-H3), 0.95(d, J=6 Hz, 21-H3), 1.18 (s, 19-H3), 5.88-6.33(4H, m, 2-,4-,6- and 7-H), 7.04(1H, d, J=10 Hz, 1-H). Anal. Calcd., For C27H34F6O2 ; C, 64.27; H, 6.79; F, 22.59. Found, C, 64.17; H, 6.81; F, 22.34.

Provenance & Evidence