HCID 53895452, compound → HCID 53824011, compound

HRID 1089360Notes

Reaction equation

HRID 1089360 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=3)[C:11]2=[O:27])=[CH:7][CH:6]=1)=[O:4].[H][H]>[Pt].C1(C)C=CC=CC=1>[CH3:26][O:25][C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH:16]=[C:12]2[CH2:13][CH2:14][CH2:15][C:10](=[CH:9][C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:29][CH:28]=3)[C:11]2=[O:27])=[CH:22][CH:21]=1)=[O:24].[CH3:26][O:25][C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH:16]=[C:12]2[CH2:13][CH2:14][CH2:15][C:10](=[CH:9][C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:29][CH:28]=3)[CH:11]2[OH:27])=[CH:22][CH:21]=1)=[O:24]

Participants

6

Reactant 2

HCID 53895452HCID 53895452, compoundHCID 178418361HCID 178418361, compound2×

Product 2

HCID 53824011HCID 53824011, compoundHCID 53895452HCID 53895452, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
175 °C

Procedure

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.

Workup

  1. temperatureThe autoclave is maintained at 175° C.
  2. temperaturecooled
  3. customThe contents of the autoclave are transferred to a round bottom flask
  4. customthe solvent removed
  5. dissolutionThe residue is dissolved in a minimum of methylene chloride
  6. customthe products separated

Sources & evidence

ORD record
ord-c10f54ccc5de4841bb4205081ffee290
Source dataset
uspto-grants-1990_10
Patent number
US04965399

Reaction notes

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