Pyridine → 3-acetylphenyl benzoate

HRID 2389280Notes

Reaction equation

HRID 2389280 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].N1C=CC=CC=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:2]([C:4]1[CH:9]=[C:8]([O:10][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 84873-HydroxyacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 2661113-acetylphenyl benzoateYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, 3-hydroxyacetophenone (0.68 g, 5 mmol) was dissolved in dichloromethane (5 mL), and pyridine (2.0 mL, 25 mmol) and benzoyl chloride (0.70 mL, 6.0 mmol) were added thereto, and then, the mixture was stirred at room temperature for 4 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a 2 mol/L aqueous sodium hydroxide solution, 2 mol/L hydrochloric acid, and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 50/50) to give benzoic acid (3-acetylphenyl)ester (1.19 g, 4.96 mmol, yield: 99%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with a 2 mol/L aqueous sodium hydroxide solution, 2 mol/L hydrochloric acid, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 50/50)

Sources & evidence

ORD record
ord-0adcb0520a024ea4a7c34a8f2a8e46e1
Source dataset
uspto-grants-2012_09
Patent number
US08273738B2

Reaction notes

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