Acetic Acid → 2-(1H-Pyrrol-1-Yl)Phenol

HRID 259032Notes

Reaction equation

HRID 259032 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].O1CCOCC1.C(O)(=O)C>CCCCCC>[OH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:10]1[CH:3]=[CH:7][CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 58012-AminophenolHCID 312751,4-DioxaneHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 2,5-dimethoxytetrahydrofuran (39.6 g), o-aminophenol (36 g), dioxane (300 ml), and glacial acetic acid (180 ml) are heated under reflux for 4 hr. The solvents are removed and the residue distributed between ethyl acetate and 5% NaHCO3. The organic phase is washed with water, dried (MgSO4), filtered, and evaporated. The dark oily residue is subjected to chromatography on 2 kg of silica and eluted with chloroform to afford an oil. After being covered with hexane and stored for several days, the oil solidifies giving the title compound, m.p. 52° - 54° C. (Reported m.p. by Artico, et al., cited above, 45° - 47° C).

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 4 hr
  3. customThe solvents are removed
  4. washThe organic phase is washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. washeluted with chloroform
  9. customto afford an oil
  10. waitstored for several days

Sources & evidence

ORD record
ord-0a857e544f46474ebf4db6188410f1b2
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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