Hydrochloric Acid → 2-Benzoyl-4,5-dimethoxybenzoic acid

HRID 54976

Reaction equation

HRID 54976 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[O:11])[O:9][C:7](=[O:8])[C:6]2=[CH:12][C:13]=1[O:14][CH3:15].[C:16]1([Mg]Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+].Cl>C1COCC1>[C:7]([C:6]1[CH:12]=[C:13]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:10]([OH:9])=[O:11])(=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 6103565,6-Dimethoxy-1,3-dihydro-2-benzofuran-1,3-dioneHCID 178478979HCID 178478979, compound

Product 1

HCID 199571592-Benzoyl-4,5-dimethoxybenzoic acidYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Thirty grams (0.14 mole) of 4,5-dimethoxyphthalic anhydride was suspended in 300 mL of THF and 87 mL (0.17 mole) of phenylmagnesium chloride in THF was added over two hours. The reaction was stirred at room temperature for 14 hours, refluxed for two hours, cooled and poured into saturated ammonium chloride. The mixture was made acidic with 6N HCl, extracted into chloroform, dried over magnesium sulfate, concentrated to provide 30 g of 2-benzoyl-4,5-dimethoxybenzoic acid.

Workup

  1. temperaturerefluxed for two hours
  2. temperaturecooled
  3. extractionextracted into chloroform
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43f8f20b41bd492a896d88ca1f42014d
Source dataset
uspto-grants-1997_04
Patent number
US05624922

Linked notes

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