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Acetic Acid → Pyrogallol triacetate

HRID 1680761
Notes
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Reaction equation

HRID 1680761 reaction equation
[C:1]1(=NO)[CH2:6][CH2:5][CH2:4][C:3](=NO)[C:2]1=[O:9].[C:12]([OH:15])(=[O:14])[CH3:13].[C:16]([O:19]C(=O)C)(=[O:18])[CH3:17].N1[CH:28]=[CH:27]C=CC=1.[OH2:29]>>[C:12]([O:15][C:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:19][C:16](=[O:18])[CH3:17])[C:2]=1[O:9][C:27](=[O:29])[CH3:28])(=[O:14])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 962Water2×HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68261391,2,3-Cyclohexanetrione, 1,3-dioxime

Product 1

HCID 10678Pyrogallol triacetateYield 0.5%

Procedure

To cyclohexane-1,2,3-trione 1,3-dioxime (100 parts) were added glacial acetic acid (400 parts) and water (1600 parts) and the mixture refluxed for four hours at 100°-100.5° C. The pyrogallol was extracted and purified as follows. 47.3% NaOH solution (483 parts) was added to the cooled mixture, when the pH rose from 3.4 to 6.0. The mixture was filtered giving insolubles (60 parts), and the filtrate was continuously extracted with ether. The extract was dried over Na2SO4 and evaporated. The residue was triturated with water and the mixture filtered giving insolubles (8 parts) and a filtrate which was evaporated on a water bath to give a tar (8 parts). To this tar were added glacial acetic acid (42 parts) and acetic anhydride (70 parts) and a catalytic amount of pyridine. After standing at room temperature for five hours, the mixture was drowned out in water and the tar obtained recrystallised from methanol (8 parts) to give pyrogallol triacetate (1 part), melting point 161°-163° C., (0.5% yield).

Workup

  1. temperaturethe mixture refluxed for four hours at 100°-100.5° C
  2. extractionThe pyrogallol was extracted
  3. custompurified
  4. addition47.3% NaOH solution (483 parts) was added to the cooled mixture, when the pH
  5. filtrationThe mixture was filtered
  6. customgiving insolubles (60 parts)
  7. extractionthe filtrate was continuously extracted with ether
  8. dry with materialThe extract was dried over Na2SO4
  9. customevaporated
  10. customThe residue was triturated with water
  11. filtrationthe mixture filtered
  12. customgiving insolubles (8 parts)
  13. customa filtrate which was evaporated on a water bath
  14. customto give a tar (8 parts)
  15. customthe tar obtained
  16. customrecrystallised from methanol (8 parts)

Sources & evidence

ORD record
ord-dcefd63704d9494bb5320c57d376a114
Source dataset
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04275247

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes