Hydroquinone → 4-Methoxyphenol

HRID 380781Notes

Reaction equation

HRID 380781 reaction equation
[C:1]1(C=CC(O)=CC=1)O.O.[OH-].[Li+].C[C:13]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=1[OH:15].[CH3:21]C1C(C)=C(C=CC=1O)O.[CH3:31][C:32]1[C:33]([OH:41])=[C:34]([CH3:40])[C:35]([CH3:39])=[C:36]([CH:38]=1)[OH:37]>CO>[CH3:31][C:32]1[C:33]([OH:41])=[C:34]([CH3:40])[C:35]([CH3:39])=[C:36]([OH:37])[C:38]=1[CH3:1].[CH3:21][O:20][C:18]1[CH:19]=[CH:13][C:14]([OH:15])=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 785Hydroquinone2×HCID 7253MethylhydroquinoneHCID 12785TrimethylhydroquinoneHCID 691002,3-DimethylhydroquinoneHCID 168937Lithium hydroxide, monohydrate

Product 2

HCID 90154-MethoxyphenolHCID 136346Durohydroquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 4.5 ml, made of SUS 316, without manometer) were charged 0.031 g of hydroquinone, 1.370 g of methanol and 0.063 mg of lithium hydroxide monohydrate (manufactured by Wako Pure Chemical Ind., Ltd.). The reaction was started by elevating the temperature up to 420° C. with sand bath. After 7 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 72% by mole, the selectivity of monomethylhydroquinone was 34% by mole, the selectivity of dimethylhydroquinone was 42% by mole and the selectivity of trimethylhydroquinone was 18% by mole. As byproducts, tetramethylhydroquinone and p-methoxyphenol were produced with selectivities of 2% by mole and 1% by mole, respectively.

Workup

  1. customup to 420° C.
  2. temperaturethe autoclave was quickly cooled

Sources & evidence

ORD record
ord-1f60ddf478334f48af70da27ac33a8d0
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Reaction notes

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