Phthalic Anhydride → 2-(2-Thienylcarbonyl)benzoic acid

HRID 1081327Notes

Reaction equation

HRID 1081327 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Cl-].[Al+3].[Cl-].[Cl-].[S:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>ClCCl>[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8030ThiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2826542-(2-Thienylcarbonyl)benzoic acidYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of phthalic anhydride (2.96 g), dichloromethane (10 ml) and aluminum chloride (5.87 g) was added a solution of thiophene (1.6 g) in dichloromethane, in limited amounts, while stirring at room temperature, then the reaction mixture was stirred for one hour at room temperature. The reaction mixture was poured into HCl-ice water, followed by extraction with ethyl acetate. The extract solution was washed with water and dried, then the solvent was distilled off to leave 2-(2-thienylcarbonyl)benzoic acid as colorless crystals (2.72 g).

Workup

  1. stirringthe reaction mixture was stirred for one hour at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with water
  4. customdried
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2962e87f8c1945adb12bf8eab97da383
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

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