Benzoic Acid → 3-oxobutan-2-yl benzoate

HRID 1290822Notes

Reaction equation

HRID 1290822 reaction equation
Cl[CH:2]([CH3:6])[C:3](=[O:5])[CH3:4].[C:7]([OH:15])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(#N)C>[C:7]([O:15][CH:2]([CH3:6])[C:3](=[O:5])[CH3:4])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 200263-Chloro-2-butanone

Product 1

HCID 2319833-oxobutan-2-yl benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-chlorobutanone (10.6 g), benzoic acid (15.0 g), triethylamine (30 ml) and acetonitrile (100 ml) was heated under reflux for 1 hour 30 minutes. The mixture was cooled and filtered to remove precipitated triethylamine hydrochloride. The acetonitrile was removed from the filtrate under reduced pressure and the residue dissolved in ethyl acetate and washed with water. The organic extracts were dried over magnesium sulphate, filtered over active carbon and the solvent was removed from the filtrate under reduced pressure, to give a yellow oil of 3-benzoyloxybutan-2-one. Yield 16.7 g. The oil was used directly without further purification in the next step.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour 30 minutes
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customto remove
  6. customprecipitated triethylamine hydrochloride
  7. customThe acetonitrile was removed from the filtrate under reduced pressure
  8. dissolutionthe residue dissolved in ethyl acetate
  9. washwashed with water
  10. dry with materialThe organic extracts were dried over magnesium sulphate
  11. filtrationfiltered over active carbon
  12. customthe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-9b21958bae674b96a195899ade3e7919
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

Loading…