Diethyl Ether → HCID 54522175, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-hydroxy-dibenzo[a,e]cyclooctene (2.3 g) in dry dichloromethane (100 ml) was added pyridinium dichromate (5.75 g) and crushed 4 A molecular sieves (3 g). After stirring at room temperature for 14 h, 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 chromotagraphy on flash silica with 5% ethyl acetate in hexane as eluent to give as a colourless solid. the title compound (2.1 g, m.p. 121°-123° C.). δ (360 MHz, CDCl3) 4.03 (2H, s, CH2), 6.92 (1H, d, J=12.8 Hz, CHA =CHB), 7.09 (1H, d, J=12.8 Hz, CHa =CHB), 7.20-7.56 (6H, m, ArH), 8.08 (1H, d, J=8.5 Hz, BrC=CH--CH= C--C=O). m/e 300 and 298 (M+).

Provenance & Evidence