p-Toluenesulfonic acid → (1,5-Dimethyl-1H-pyrrol-3-yl)(4-methylphenyl)methanone

HRID 1414739Notes

Reaction equation

HRID 1414739 reaction equation
[CH3:1][N:2]1[C:6](C(C2C=CC(C)=CC=2)=O)=[CH:5][CH:4]=[C:3]1[CH3:16].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.[C:28](=[O:31])(O)[O-].[Na+]>>[CH3:1][N:2]1[CH:6]=[C:5]([C:28]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)=[O:31])[CH:4]=[C:3]1[CH3:16]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 12648628(1,5-Dimethyl-1H-pyrrol-2-yl)(4-methylphenyl)methanone

Product 1

HCID 12648631(1,5-Dimethyl-1H-pyrrol-3-yl)(4-methylphenyl)methanone

Procedure

A 1.0g sample of 1,2-dimethyl-5-p-toluoylpyrrole in 10g of dried p-toluenesulfonic acid heated at 105° C for 1 hour. The solution is then poured into sodium bicarbonate solution and extracted into chloroform. The chloroform is evaporated in vacuo and the residue is recrystallized from ethyl acetate to give 1,2-dimethyl-4-p-toluoylpyrrole as a tan solid; m.p. 117°-119° C.

Workup

  1. extractionextracted into chloroform
  2. customThe chloroform is evaporated in vacuo
  3. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fb857c9ae75747ef8f872f0616f87a7a
Source dataset
uspto-grants-1977_01
Patent number
US04002643

Reaction notes

Loading…