Hydrochloric Acid → O-(p-Anisoyl)benzoic acid

HRID 54974Notes

Reaction equation

HRID 54974 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.[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH3:19][O:18][C:12]1[CH:17]=[CH:16][C:15]([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:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 7519AnisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 231963O-(p-Anisoyl)benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 57 g (0.4 mole) of phthalic anhydride and 43 mL (0.4 mole) of anisole in 400 mL of benzene was treated with 105 g (0.8 mole) of aluminum chloride at 5°. The reaction was kept for five days at 5°, poured into 600 mL of 2N aqueous HCl and ice and filtered. The residue was triturated in aqueous sodium carbonate and filtered repeatedly until the solid no longer contained product. The sodium carbonate extracts were combined, washed with ether, and acidified with 2N aqueous HCl. The product was extracted into ether, dried over sodium sulfate and stripped. It was recrystallized from toluene to provide 80% yield of product, mp 145-147.

Workup

  1. filtrationfiltered
  2. customThe residue was triturated in aqueous sodium carbonate
  3. filtrationfiltered repeatedly until the solid no longer contained product
  4. washwashed with ether
  5. extractionThe product was extracted into ether
  6. dry with materialdried over sodium sulfate
  7. customIt was recrystallized from toluene

Sources & evidence

ORD record
ord-b80fd843b7e24e349059778f1d85dc1d
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Reaction notes

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