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

HRID 572520Notes

Reaction equation

HRID 572520 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:13]1(=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15](=[O:22])[O:14]1>>[CH3:8][C:1]1[CH:2]=[C:3]([CH3:7])[CH:4]=[CH:5][C:6]=1[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:13]([OH:23])=[O:14])=[O:22]

Participants

4

Reactant 3

HCID 6811Phthalic AnhydrideHCID 7929M-XyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2466092-(2,4-Dimethylbenzoyl)benzoic acidYield 97%

Procedure

An ice/salt cold mixture of m-xylene (114 g, 1073 mmol) was treated with aluminium chloride (59.4 g, 446 mmol) (in three portions), followed by 2-benzofuran-1,3-dione (30 g, 203 mmol) (in three portions). The mixture was warmed to room temperature and stirred for 3 hours after which time the mixture turned to a thick white suspension. The mixture was heated to 55° C. for 2 hours, and cooled to room temperature. The thick mixture was slowly poured into ice cold 20% HCl and collected on filter paper. The filtered material was allowed to dry to give the desired product as a white solid (50 g, 97%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.98-8.07 (m, 1 H) 7.60-7.69 (m, 1 H) 7.51-7.59 (m, 1 H) 7.38-7.45 (m, 1 H) 7.01-7.13 (m, 2 H) 6.86-6.94 (m, 1 H) 2.61 (s, 3 H) 2.33 (s, 3 H); LC/MS (m/z) ES+=255 (M+1).

Workup

  1. temperatureThe mixture was heated to 55° C. for 2 hours
  2. temperaturecooled to room temperature
  3. customcollected
  4. filtrationon filter paper
  5. customto dry

Sources & evidence

ORD record
ord-e9afc619b1904892836434ffa73c0c6c
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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