Phthalic Anhydride → 2-(4'-Chlorobenzoyl)benzoic acid

HRID 615662

Reaction equation

HRID 615662 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:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 665642-(4'-Chlorobenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution prepared by adding 30 g (0.2 mol.) of phthalic anhydride to 122 ml of dried chlorobenzene, was added 64 g (0.48 mol.) of well-ground anhydrous aluminium chloride with stirring. The reaction temperature rose gradually, and the reaction system reached a refluxing condition. The refluxing was continued for 1 hour as the reaction temperature was controlled so that the reaction system refluxed moderately using the ice bath. Then, the reaction product solidified spontaneously. 300 ml of water was added dropwise to the reaction system while cooling by means of an ice bath. The thus produced white precipitate was thoroughly washed with water and cooled ethanol to obtain 45 g of crude crystals. These crude crystals were recrystallized from benzene to obtain the intended compound. Yield 38 g, Melting Point 146° to 148° C.

Workup

  1. customTo a solution prepared
  2. temperaturerefluxed moderately
  3. temperaturewhile cooling by means of an ice bath
  4. washThe thus produced white precipitate was thoroughly washed with water
  5. temperaturecooled ethanol

Sources & evidence

ORD record
ord-32bc8f3a6462456696a6fbda4f1bf644
Source dataset
uspto-grants-1985_02
Patent number
US04500636

Linked notes

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