Oxygen → Methyl-1,4-benzoquinone

HRID 727481

Reaction equation

HRID 727481 reaction equation
O=O.[CH3:3][C:4]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=1[OH:6].S(=O)(=O)(O)O>C(O)(=O)C>[CH3:3][C:4]1[C:5](=[O:6])[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1

Participants

5

Reactant 3

HCID 977Oxygen2×HCID 1118Sulfuric AcidHCID 7253Methylhydroquinone

Product 1

HCID 11122Methyl-1,4-benzoquinoneYield 61.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

Oxygen was passed into a solution of 0.68 g (2 mmol) of iron 5,14-dihydrodibenzo[b,i][5,9,14,18]tetraaza[14]annulene in 150 ml of 85% by weight aqueous acetic acid and, during this, a solution of 12.4 g (100 mmol) of methylhydroquinone and 0.5 g of concentrated sulfuric acid in 75 ml of 85% by weight acetic acid was added dropwise while stirring vigorously at 40° C. After oxygen up-take ceased, the mixture was subjected to a steam distillation. The distillate was extracted with tert-butyl methyl ether. The organic phase was shaken with aqueous sodium bicarbonate solution and then with water, separated from the aqueous phase, dried over magnesium sulfate, filtered and evaporated to dryness to yield 7.5 g (46%) of 2-methylbenzoquinone in the form of a yellow powder. Melting point 66°-68° C.

Workup

  1. distillationthe mixture was subjected to a steam distillation
  2. extractionThe distillate was extracted with tert-butyl methyl ether
  3. stirringThe organic phase was shaken with aqueous sodium bicarbonate solution
  4. customwith water, separated from the aqueous phase
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-5e6a35ae7d31484597e3dd3d9eaeb9f3
Source dataset
uspto-grants-1998_01
Patent number
US05712416

Linked notes

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