p-Toluenesulfonic acid → Methyl 3-benzoylbenzoate

HRID 332688

Reaction equation

HRID 332688 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.[CH3:18]C1C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH3:18])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 1013863-Benzoylbenzoic acid

Product 1

HCID 349621Methyl 3-benzoylbenzoateYield 905.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 3-benzoylbenzoic acid (10.0 g, 44.4 mmol) and p-TSA (0.85 g, 4.39 mmol) in methanol (200 mL) was heated at 75° C. for 18 hours. The reaction mixture was allowed to cool, and the solvent evaporated at reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was evaporated at reduced pressure to afford the title compound (9.55 g, 90%).

Workup

  1. temperatureto cool
  2. customthe solvent evaporated at reduced pressure
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  4. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-d39238a40f694b9b81a0d9f53718ff8e
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Linked notes

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