Methanol → Methyl o-benzoylbenzoate

HRID 2268691Notes

Reaction equation

HRID 2268691 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O:13][CH3:18])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 68132-Benzoylbenzoic Acid2×

Product 1

HCID 11816Methyl o-benzoylbenzoate

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

The ester methyl 2-benzoylbenzoate was prepared from the corresponding acid 2-benzoyl benzoic acid by Fischer esterification. One mole (226.23 grams) of 2-benzoylbenzoic acid was refluxed overnight in 1500 milliliters of methanol containing 2 grams of p-toluenesulfonic acid as catalyst. Cooling and rotary evaporation of the solvent afforded the ester as white crystals (melting point 145° C.) having a purity of about 99 percent. This material was used as such without further purification. Other esters can be prepared from their corresponding acids in a similar fashion.

Workup

  1. temperatureCooling
  2. customrotary evaporation of the solvent

Sources & evidence

ORD record
ord-24bc3f6971fd47a79decc3d4796a1783
Source dataset
uspto-grants-2001_12
Patent number
US06328793B1

Reaction notes

Loading…