Trimethyl cyclohex-5-ene-1,2,4-tricarboxylate → Trimethyl cyclohexane-1,2,4-tricarboxylate

HRID 1970210Notes

Reaction equation

HRID 1970210 reaction equation
[CH:1]1([C:15]([O:17][CH3:18])=[O:16])[CH:6]=[CH:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:2]1[C:11]([O:13][CH3:14])=[O:12].[H][H]>C(Cl)Cl.[Pd]>[CH:1]1([C:15]([O:17][CH3:18])=[O:16])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:2]1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 60136166Trimethyl cyclohex-5-ene-1,2,4-tricarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12616206Trimethyl cyclohexane-1,2,4-tricarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of trimethyl cyclohex-5-ene-1,2,4-tricarboxylate (0.50 g, 1.9 mmol) in methylene chloride (15 ml) containing a catalytic amount of palladium on carbon (150 mg, 5 percent Pd/C, 7.5 mg Pd, 4 mole percent) is stirred at room temperature under balloon pressure of hydrogen gas for 2 hours, at which point GC-MS analysis shows complete conversion. Filtration and removal of the solvent provides trimethyl cyclohexane-1,2,4-tricarboxylate as a clear, colorless gel (0.42 g, 1.6 mmol, 85 percent yield).

Workup

  1. filtrationFiltration and removal of the solvent

Sources & evidence

ORD record
ord-9df57007d1ad4d998b107a24f0eb91fe
Source dataset
uspto-grants-2013_04
Patent number
US08426639B2

Reaction notes

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