Phthalic Anhydride → 2-(2,4-dichlorobenzoyl)benzoic acid

HRID 615663Notes

Reaction equation

HRID 615663 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]=[C:15]([Cl:19])[CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:12][C:13]1[CH:14]=[C:15]([Cl:19])[CH:16]=[CH:17][C:18]=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 109431,3-DichlorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3504822-(2,4-dichlorobenzoyl)benzoic acidYield 54.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution prepared by adding 30 g (0.2 mol.) of phthalic anhydride to 146 g (1.0 mol.) of dried 1,3-dichlorobenzene, was added 64 g (0.48 mol.) of well-ground anhydrous aluminium chloride with stirring. The mixture was heated and stirred for 3 hours on the oil bath kept at 120° C. Thereafter, the reaction mixture was sufficiently cooled on an ice bath and thereto, 100 ml of water was added dropwise. The thus produced white precipitate was thoroughly washed with successive, water and cooled ethanol to obtain 32 g of crude crystals. These crude crystals were recrystallized from benzene to obtain the marked compound. Yield 24 g, Melting Point 178° to 181° C.

Workup

  1. customTo a solution prepared
  2. temperatureThe mixture was heated
  3. stirringstirred for 3 hours on the oil bath
  4. customkept at 120° C
  5. temperatureThereafter, the reaction mixture was sufficiently cooled on an ice bath
  6. washThe thus produced white precipitate was thoroughly washed with successive, water
  7. temperaturecooled ethanol

Sources & evidence

ORD record
ord-b3e2bbf23be64323b70ccb89148efd25
Source dataset
uspto-grants-1985_02
Patent number
US04500636

Reaction notes

Loading…