Diethyl Ether → HCID 54476367, compound

Participants

Reaction Steps

To a solution of 1-chloro-5-hydroxy-dibenzo[a,e]cyclooctene (1.5 g) in dry dichloromethane (60 ml) was added pyridinium dichromate (5.0 g) and crushed 4A molecular sieves (2.5 g). After stirring at room temperature for 3h. diethyl ether (150 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 10% ethyl acetate in hexane as eluent to give the title compound (1.35 g) m.p. 151°-153° C. δ(360 MHz, CDCl3) 4.09 (2H, s, CH2 --C=O). 7.06 (1H, d, J=11.9 Hz, ArCHA =CHBAr), 7.18 (1H, d, J=11.9 Hz, ArCHA =CHBAr), 7.20-7.30 (5H, m, aromatics), 7.50 (1H, dd, J=7.8 and 1.4 Hz, CH=CCl) and 7.86 (1H, dd, J=8.0 and 1.3 Hz, CH=C--C=O). m/e 254 (M+). i.r. (νmax, nujol) 1670 cm-1 (CO). Found: C, 75.1; H, 4.6. C16H11C10 requires: C, 75.4; H, 4.4%.

Provenance & Evidence