Benzoic Acid → 3-(Benzoyloxy)-2,4-pentanedione

HRID 1511117Notes

Reaction equation

HRID 1511117 reaction equation
[OH-].[K+].[C:3]([OH:11])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C=O)C.Cl[CH:18]([C:22](=[O:24])[CH3:23])[C:19](=[O:21])[CH3:20]>O>[C:3]([O:11][CH:18]([C:22](=[O:24])[CH3:23])[C:19](=[O:21])[CH3:20])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 743283-Chloro-2,4-pentanedione

Product 1

HCID 207383-(Benzoyloxy)-2,4-pentanedioneYield 96.12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A flask was charged with powdered potassium hydroxide (21.89 g, 390.2 mmol), benzoic acid (47.65 g, 390.2 mmol), and DMF (500 mL). The mixture was heated at 50° C. for 1 hour. 3-Chloropentane-2,4-dione (52.5 g, 390.2 mmol) was added and the reaction was stirred at 50° C. overnight. The reaction was cooled to ambient temperature, diluted in water (1.5 L) and extracted with ether (3×500 mL). The combined organic layers were washed with water, saturated NH4Cl and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 2,4-dioxopentan-3-yl benzoate (82.59 g, 96.12% yield) as yellow oil.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with ether (3×500 mL)
  3. washThe combined organic layers were washed with water, saturated NH4Cl and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edf2748695894940907f3135946a040e
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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