Hydroquinone → Durohydroquinone

HRID 380782Notes

Reaction equation

HRID 380782 reaction equation
[C:1]1(C=CC(O)=CC=1)O.[O-2].[Ca+2].CC1C=C(O)C=CC=1O.CC1C(C)=C(C=CC=1O)O.[CH3:30][C:31]1[C:32]([OH:40])=[C:33]([CH3:39])[C:34]([CH3:38])=[C:35]([CH:37]=1)[OH:36]>CO>[CH3:30][C:31]1[C:32]([OH:40])=[C:33]([CH3:39])[C:34]([CH3:38])=[C:35]([OH:36])[C:37]=1[CH3:1]

Participants

7

Reactant 5

HCID 785Hydroquinone2×HCID 7253MethylhydroquinoneHCID 12785TrimethylhydroquinoneHCID 691002,3-DimethylhydroquinoneHCID 6850728Calciumoxide

Product 1

HCID 136346Durohydroquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 4.5 ml, made of SUS 316, without manometer) were charged 0.016 g of hydroquinone, 1.355 g of methanol and 2.5 mg of calcium oxide (manufactured by Wako Pure Chemical Ind., Ltd.). The reaction was started by elevating the temperature up to425° C. with sand bath. After 8 minutes, the autoclave was quickly cooled and the reaction solution was taken out from the autoclave when the temperature was cooled back to the room temperature. The measurement according to the process described above revealed that the conversion of hydroquinone was 87% by mole, the selectivity of monomethylhydroquinone was 30% by mole, the selectivity of dimethylhydroquinone was 42% by mole and the selectivity of trimethylhydroquinone was 18% by mole. As byproducts, tetramethylhydroquinone was produced with a selectivity of 3% by mole.

Workup

  1. temperaturethe autoclave was quickly cooled

Sources & evidence

ORD record
ord-e5892577487542c3aee56a62eb3928f9
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Reaction notes

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