Diethyl Ether → HCID 53979940, compound

Participants

Reaction Steps

To a solution of 2-methoxy-6-hydroxy-dibenzo[a,e]cyclooctene (1.5 g) in dry dichloromethane (100 ml) was added pyridinium dichromate (4.5 g) and crushed 4A molecular sieves (2.3 g). After stirring at room temperature for 2h, diethyl ether (200 ml) was added and the reaction mixture was filtered through a plug of celite. The solvent was removed in vacuo and the residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent to give, as a colourless solid, the title compound (1.4 g), m.p. 104°-106° C. δ(360 MHz, CDCl3), 3.75 (3H, s, CH3O), 3.99 (2H, s, CH2 --CO), 6.73 (1H, d, J=2.7 Hz, CH=(OCH3)--CH), 6.86 (1H, dd, J=8.5 and 2.7 Hz, CH=C(OCH3)--CH), 7.01 (2H, s, Ar--CH=CH--Ar), 7.29-7.51 (4H, m, aromatics) and 8.24 (1H, dd, J=8.0 and 1.4 Hz, CH=C--CO). m/e 250 (M+). i.r. (νmax, nujol) 1665 cm-1 (CO). Found: C,81.5; H, 5.6. C17H14O2 requires: C, 81.0; H, 5.8%

Provenance & Evidence