4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 20 ml methanol was dissolved 500 mg/2.0 mmol of bis(4-hydroxy-3,5-dimethylphenyl)methane, and 886 mg/4.0 mmol of dicyanodichloroquinone was added to the solution at once in a stream of argon. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the insoluble matter was separated by filtration and re-concentrated. The resulting crude product was purified by silica gel column chromatography using methylene chloride for the eluting solution to obtain 230 mg of the desired 4,4'-dihydroxy-3,3',5,5'-tetramethylbenzophenone. MS: 270 (M+), 1H-NMR (CDCl3 /DMSO-d6): δ2.29 (12H, s), 7.41 (4H, s), 7.96 (2H, s). was added to the solution at once in a stream of argon the solvent was distilled off under reduced pressure The residue was dissolved in ethyl acetate the insoluble matter was separated by filtration re-concentrated The resulting crude product was purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 20 ml methanol was dissolved 500 mg/2.0 mmol of bis(4-hydroxy-3,5-dimethylphenyl)methane, and 886 mg/4.0 mmol of dicyanodichloroquinone was added to the solution at once in a stream of argon. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, and the insoluble matter was separated by filtration and re-concentrated. The resulting crude product was purified by silica gel column chromatography using methylene chloride for the eluting solution to obtain 230 mg of the desired 4,4'-dihydroxy-3,3',5,5'-tetramethylbenzophenone. MS: 270 (M+), 1H-NMR (CDCl3 /DMSO-d6): δ2.29 (12H, s), 7.41 (4H, s), 7.96 (2H, s). was added to the solution at once in a stream of argon the solvent was distilled off under reduced pressure The residue was dissolved in ethyl acetate the insoluble matter was separated by filtration re-concentrated The resulting crude product was purified by silica gel column chromatography