Acetone → HCID 12340623, compound

HRID 259041Notes

Reaction equation

HRID 259041 reaction equation
O.[C:2]1(C)[CH:7]=CC(S(O)(=O)=O)=C[CH:3]=1.O.[OH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.CC(C)=O>C1C=CC=CC=1>[CH3:3][C:2]1([CH3:7])[C:22]2=[CH:23][CH:24]=[CH:25][N:21]2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 7123342-(1H-Pyrrol-1-Yl)Phenol

Product 1

HCID 12340623HCID 12340623, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

p-Toluenesulfonic acid monohydrate (110 mg) is dissolved in 70 ml of dry benzene and the solution heated at reflux with a water-separator for about 10 minutes. A solution of 1-(o-hydroxyphenyl)-pyrrole (1.1 g) in dry benzene (80 ml) is added, followed by 10 ml of acetone. The reaction mixture is heated at reflux with the water-separator for 15 hr, cooled, and washed with a solution of NaHCO3. The benzene solution is evaporated to dryness. The residue is subjected to chromatography on silica gel, using chloroform as eluent. Evaporation of the first portion of the eluate gives the title compound, m.p. 38° - '° C, νmaxCHCl3 1600, 1510, 1345 cm-1.

Workup

  1. temperaturethe solution heated
  2. temperatureThe reaction mixture is heated
  3. temperaturecooled
  4. washwashed with a solution of NaHCO3
  5. customThe benzene solution is evaporated to dryness
  6. customEvaporation of the first portion of the eluate

Sources & evidence

ORD record
ord-30164572fc744f6e8990d6f64883ea67
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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