[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:17])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][OH:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O-][Si]([O-])=O.[Mg+2].[CH2:34]([O:36]CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:17])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:36][CH3:34])=[CH:13][CH:12]=1)[CH:5]=[O:6]To an ice-cold solution of 3,5-dichloro-4-phenoxybenzyl alcohol (200 mg, 0.67 mmol) in 6.7 ml of dichloromethane with 4 A sieves was added a mixture of pyridinium chlorochromate (317 mg, 1.47 mmol) and celite (317 mg). The reaction mixture was brought to room temperature and stirred for 1 h then diluted with diethyl ether and passed through a column of florisil. Removal of volatiles in vacuo afforded the title compound as a solid (175 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 9.93 (s, 1H), 7.91 (s, 2H), 6.83 (d, j=6.8 Hz, 2H), 6.77 (d, j=6.8 Hz, 2H), 3.77 (s, 3H). M+1=297.
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