Water → HCID 54176247, compound

Participants

Reaction Steps

16.7 g (70 mmol) of crude (4-Hydroxyimino-3-methyl-cyclohexa-2,5-dienylidene)-phenylacetonitrile are dissolved in 100 ml of THF and cooled in an ice bath. After adding 6.0 ml (77 mmol) of methanesulfonyl chloride, 14.8 ml (106 mmol) of triethylamine are added dropwise to the solution, keeping the temperature below 10° C. The reaction mixture is stirred in the ice bath for 30 min., poured into 250 ml of iced water, and extracted with ethyl acetate. The organic phase is washed with 0.2 N hydrochloric acid, water, and saturated aqueous sodium chloride. The organic phase is dried over MgSO4, the solvent is distilled off, and the residue is purified by recrystallization from toluene. 11.5 g (52%) of (3-Methyl-4-methylsulfonyloxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of bright yellow crystals having a melting point of 136-138° C.(dec.).

Provenance & Evidence