Water → HCID 14116044, compound

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Reaction Steps

The hydrocarbon (5) 48 mg; 0.22 mmol) was dissolved in hot acetic acid (15 ml) and water (5 ml) was added slowly with stirring to maintain homogeneity of the solution. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (198 mg, 0.88 mmol) was added, changing the color of the solution to dark green. Stirring was continued at reflux for 30 min. during which time the color of the solution changed to dark red. The reaction mixture was cooled and diluted with ether, and the ether layer was washed with water and aqueous NaOH. The solution was dried over MgSO4 and evaporated to provide a white solid which was chromatographed on a column of Florisil™. Elution with ether yielded 6 (39 mg, 76%):m.p. 127°-128° C.; NMR δ272 (t,l,H15 or16), 2.85-2.91 (m,4,H6,7), 3.07 (t,l,H15 or16), 7.24-7.31 (m,3,H2,3,4), 7.67-7.77 (m,3,H1,11,12) Anal. Calc'd. for C17H14O: C,87.25; H,6.02. Found: C,87.13; H,6.03.

Provenance & Evidence