Methanol → Methyl 3-benzoylbenzoate

HRID 2184324Notes

Reaction equation

HRID 2184324 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:23]O>C(OCC)(=O)C>[CH3:23][O:13][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1013863-Benzoylbenzoic acid

Product 1

HCID 349621Methyl 3-benzoylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Benzoyl-benzoic acid (5.12 g, 22.6 mmol) was stirred in methanol (45 mL) with conc. H2SO4 (2.0 mL) for 18 h at 60° C. The reaction mixture was diluted with ethyl acetate and then washed with an aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered, and concentrated to provide 3-benzoyl-benzoic acid methyl ester (5.4 g, 22.6 mmol) in quantitative yield as a yellow oil.

Workup

  1. washwashed with an aqueous NaHCO3 solution
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-03731bebb93a432aab22d224d6568222
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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