2-Aminophenol → 2-(1H-Pyrrol-1-Yl)Phenol

HRID 1287316Notes

Reaction equation

HRID 1287316 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].CO[CH:11]1[CH2:15][CH2:14][CH:13](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH:11]=[CH:15][CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 7123342-(1H-Pyrrol-1-Yl)Phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

109 g of o-aminophenol and 132 g of 2,5-dimethoxy-tetrahydrofurane in 700 ml of glacial acetic acid are heated to the boil for 30 minutes. After cooling, the reaction mixture is filtered and the polymeric material is thus removed. The filtrate is evaporated in vacuo, the residue is dissolved in approx. 1 liter of ethyl acetate and the solution is washed with 200 ml of water. The dark oil which remains after drying and evaporating the organic phase is distilled in a bulb tube under a high vacuum. This gives o-(pyrrol-1-yl)-phenol of boiling point 115°-125° C/0.05 mm Hg gives an oil which gradually crystallises and melts at 46°-49° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. customthe polymeric material is thus removed
  4. customThe filtrate is evaporated in vacuo
  5. dissolutionthe residue is dissolved in approx. 1 liter of ethyl acetate
  6. washthe solution is washed with 200 ml of water
  7. customafter drying
  8. customevaporating the organic phase
  9. distillationis distilled in a bulb tube under a high vacuum

Sources & evidence

ORD record
ord-299d9f52fd53468aad7af19b9441207b
Source dataset
uspto-grants-1976_10
Patent number
US03984436

Reaction notes

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