Hydrochloric Acid → Pyrogallol

HRID 1680762Notes

Reaction equation

HRID 1680762 reaction equation
C([O:4][C:5]1[CH:18]=[CH:17][CH:16]=[C:11]([O:12]C(=O)C)[C:6]=1[O:7]C(=O)C)(=O)C.Cl>C(O)(=O)C>[C:5]1([CH:18]=[CH:17][CH:16]=[C:11]([OH:12])[C:6]=1[OH:7])[OH:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 106781,2,3-Benzenetriol, 1,2,3-triacetate

Product 1

HCID 1057PyrogallolYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 100 parts of pyrogallol triacetate as prepared above were added glacial acetic acid (364 parts) and 2 N HCl solution (3640 parts) and the mixture refluxed for three hours under a nitrogen blanket. Continuous ether extraction followed by evaporation of the extract gave an oil which slowly crystallised. Recrystallisation from toluene gave pyrogallol (44 parts, 87% yield).

Workup

  1. temperaturethe mixture refluxed for three hours under a nitrogen blanket
  2. extractionContinuous ether extraction
  3. customfollowed by evaporation of the extract
  4. customgave an oil which
  5. customslowly crystallised
  6. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-d7ffb6ca765c4ec7aefcb7a49275de6a
Source dataset
uspto-grants-1981_06
Patent number
US04275247

Reaction notes

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