Toluene → Ethyl 4-benzoylbenzoate

HRID 1935614Notes

Reaction equation

HRID 1935614 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1(C)C=CC=C[CH:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH2:18][CH3:19])=[O:14])=[CH:16][CH:17]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 691474-Benzoylbenzoic acid

Product 1

HCID 570996Ethyl 4-benzoylbenzoateYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-benzoylbenzoic acid (20 g, 88.4 mmole), toluene (5 mL), p-toluenesulfonic acid (1 g) and ethanol (20 mL) was refluxed for 12 hours, cooled, washed with 5% sodium carbonate, and neutralized by water wash. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 22 g ethyl 4-benzoylbenzoate in a yield 90.5%.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperaturecooled
  3. washwashed with 5% sodium carbonate
  4. washwash
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6fda9ca9a9644c6e8c3ce0b85a9009fa
Source dataset
uspto-grants-2002_05
Patent number
US06387942B2

Reaction notes

Loading…