2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,2-Dimethyl 4,5-dimethyl-1,2-benzenedicarboxylate

HRID 1186038

Reaction equation

HRID 1186038 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][C:9]([CH3:11])=[C:8]([CH3:12])[CH2:7][C:6]=1[C:13]([O:15][CH3:16])=[O:14])=[O:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClC1C=CC=CC=1>[CH3:16][O:15][C:13](=[O:14])[C:6]1[C:5](=[CH:10][C:9]([CH3:11])=[C:8]([CH3:12])[CH:7]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 600973Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylate

Product 1

HCID 6058061,2-Dimethyl 4,5-dimethyl-1,2-benzenedicarboxylate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 4,5-dimethyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (3.84 g, 17.1 mmol) in chlorobenzene was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (7.77 g, 34.2 mmol) at room temperature and the resulting mixture was heated to reflux 48 h. The resulting mixture was cooled and filtered through FLORISIL®. The pad of FLORISIL® was rinsed with diethyl ether and the filtrate filtered another (3×) through a pad of FLORISIL®. The filtrate was evaporated in vacuo to yield an amber syrup, which was purified via flash column chromatography (EtOAc/Heptane 4:1) to yield 4,5-dimethyl-phthalic acid dimethyl ester as a colorless oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux 48 h
  3. temperatureThe resulting mixture was cooled
  4. filtrationfiltered through FLORISIL®
  5. washThe pad of FLORISIL® was rinsed with diethyl ether
  6. filtrationthe filtrate filtered another (3×) through a pad of FLORISIL®
  7. customThe filtrate was evaporated in vacuo
  8. customto yield an amber syrup, which
  9. customwas purified via flash column chromatography (EtOAc/Heptane 4:1)

Sources & evidence

ORD record
ord-64d41f5f9fe34eb8b43a2529d3f08b65
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Linked notes

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