2,2,6,6-Tetrachlorocyclohexan-1-one → Pyrogallol

HRID 1856428Notes

Reaction equation

HRID 1856428 reaction equation
Cl[C:2]1(Cl)[CH2:7][CH2:6]CC(Cl)(Cl)[C:3]1=[O:10].[C:12]([O-:15])(=O)[CH3:13].[Na+].C(=O)(O)[O-:18].[Na+]>O>[C:12]1([CH:13]=[CH:6][CH:7]=[C:2]([OH:18])[C:3]=1[OH:10])[OH:15]

Participants

5

Reactant 3

HCID 774072,2,6,6-Tetrachlorocyclohexan-1-oneHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 1057PyrogallolYield 28.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a blanket of nitrogen were mixed 2,2,6,6-tetrachlorocyclohexanone (100 parts), sodium acetate (424 parts) and water (1,059 parts), and the mixture refluxed for 10 minutes. The mixture was then cooled to 50° C. when sodium bicarbonate (318 parts) was added giving severe foaming. The mixture was then extracted continuously with ether, the extract dried over magnesium sulphate and evaporated to give a residue (39 parts). The residue was triturated with chloroform (39 parts ) to give after filtering and drying in air 15.2 parts of pyrogallol (28.5% yield) as a tan solid, m.pt. 130.5°-133.5° C.

Workup

  1. temperaturethe mixture refluxed for 10 minutes
  2. additionwas added
  3. customgiving severe foaming
  4. extractionThe mixture was then extracted continuously with ether
  5. dry with materialthe extract dried over magnesium sulphate
  6. customevaporated
  7. customto give a residue (39 parts)
  8. customThe residue was triturated with chloroform (39 parts )
  9. customto give
  10. filtrationafter filtering

Sources & evidence

ORD record
ord-d45c15c56d8c42fba80f4e5e7a227cc0
Source dataset
uspto-grants-1980_08
Patent number
US04219505

Reaction notes

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