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

HRID 385225Notes

Reaction equation

HRID 385225 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]>C1(C)C=CC=C(C)C=1.[Pt]>[C:15]([O:17][CH3:18])(=[O:16])[C:1]1[C:2](=[CH:3][C:4](=[CH:5][CH:6]=1)[C:7]([O:9][CH3:10])=[O:8])[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 60136166Trimethyl cyclohex-5-ene-1,2,4-tricarboxylate

Product 1

HCID 17159Trimethyl 1,2,4-benzenetricarboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 7929M-XyleneSolvent

Procedure

Trimethyl cyclohex-5-ene-1,2,4-tricarboxylate (200 mg, 0.78 mmol) is mixed with 305 mg of 5 percent by weight platinum on a carbon support in m-xylene (30 ml). The reaction mixture is refluxed with the reflux apparatus being open to air for 4 days. The residual platinum on carbon is then filtered off and the filtrate is concentrated down to a clear colorless gel. The desired product is obtained with a 65 percent yield. The yield is determined by GC/MS using a dodecane as an internal standard.

Workup

  1. temperatureThe reaction mixture is refluxed with the reflux apparatus
  2. filtrationThe residual platinum on carbon is then filtered off
  3. concentrationthe filtrate is concentrated down to a clear colorless gel

Sources & evidence

ORD record
ord-1bce3db1f23940db870f1125003315b3
Source dataset
uspto-grants-2013_02
Patent number
US08367859B2

Reaction notes

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