HCID 53895452, compound → HCID 53824011, compound

Participants

Reaction Conditions

Reaction Steps

An autoclave containing 2,6-bis(4'-methoxycarbonylbenzylidene)cyclohexanone (5.0 g, 0.0128 mol), 5% platinum on carbon (0.5 g) and toluene (100 mL) is pressurized to 50 psig with hydrogen, heated to 175° C. and then pressurized with hydrogen to a total pressure of 250 psig. The autoclave is maintained at 175° C. and 250 psig for 6 hours and then cooled and vented. The contents of the autoclave are transferred to a round bottom flask and the solvent removed. The residue is dissolved in a minimum of methylene chloride and the products separated using medium pressure liquid chromatography to yield 2.73 g (0.0069 mol) of 2,6-bis(4'-methoxycarbonylbenzylidene)cyclohexanone and 1.03 g (0.0026 mol) of 2,6-bis(4'-methoxycarbonylbenzylidene)cyclohexanol. Both the ketone product [FDMS: M+/e=394; IR (CH2Cl2): 1273, 1690, 1720 cm(-1)] and the alkanol product [FDMS: M+/e=396; IR (CH2Cl2 ): 1284, 1720, 3500 (br) cm(-1)] are obtained as a mixture of the cis and trans cyclohexanol isomers which are identified on the basis of their infrared and mass spectra.

Provenance & Evidence