Benzene → HCID 18424207, compound

HRID 1606157Notes

Reaction equation

HRID 1606157 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:20](O)[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17][CH2:20][CH3:21])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 10016371HCID 10016371, compound

Product 1

HCID 18424207HCID 18424207, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 55.4 g. of 5-(p-chlorobenzoyl)-1-methyl-pyrrole-2-acetic acid, 44 ml. of absolute ethanol, 1g. of p-toluenesulfonic acid and 650 ml. of benzene is heated under reflux with azeotropic removal of water for 7 hours. The reaction mixture is filtered, washed with sodium bicarbonate solution, dried over anhyrous magnesium sulfate and the solvent evaporated in vacuo. The crystalline residue is recrystallized twice from cyclohexane to give ethyl 5-(p-chlorobenzoyl)-1-methyl-pyrrole-2-acetate as a yellow solid, m.p. 74°-76°C.

Workup

  1. additionA suspension of 55.4 g
  2. filtrationThe reaction mixture is filtered
  3. washwashed with sodium bicarbonate solution
  4. dry with materialdried over anhyrous magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe crystalline residue is recrystallized twice from cyclohexane

Sources & evidence

ORD record
ord-b9e3943720b34d35a0fb9fc59ff3edec
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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