Methylhydroquinone → Durohydroquinone

HRID 380774Notes

Reaction equation

HRID 380774 reaction equation
[CH3:1]C1C=C(O)C=CC=1O.C[O-].[Na+].CC1C(C)=C(C=CC=1O)O.[CH3:23][C:24]1[C:25]([OH:33])=[C:26]([CH3:32])[C:27]([CH3:31])=[C:28]([CH:30]=1)[OH:29]>CO>[CH3:23][C:24]1[C:25]([OH:33])=[C:26]([CH3:32])[C:27]([CH3:31])=[C:28]([OH:29])[C:30]=1[CH3:1]

Participants

6

Reactant 4

HCID 7253Methylhydroquinone2×HCID 12785TrimethylhydroquinoneHCID 691002,3-DimethylhydroquinoneHCID 10942334Sodium Methoxide

Product 1

HCID 136346Durohydroquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.108 g of methylhydroquinone, 3.573 g of methanol and 0.2 mg of sodium methylate. The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 16 MPa. After 4 hours, 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 methylhydroquinone was 86% by mole, the selectivity of dimethylhydroquinone was 38% by mole, the selectivity of trimethylhydroquinone was 37% by mole and no tetramethylhydroquinone was produced. As byproducts, methyl ethers of monomethylhydroquinone, dimethylhydroquinone and trimethylhydroquinone, represented by the formulae shown above, were formed with a selectivity of 6%, 4% and 3%, respectively.

Workup

  1. customequipped with a manometer)
  2. customup to 350° C.
  3. temperaturethe autoclave was quickly cooled

Sources & evidence

ORD record
ord-2f89a487dff242c6bbc0ea7b9ebf3e32
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Reaction notes

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