Hydrochloric Acid → 2,4-Pentanedione, 3-(2-nitrobenzoyl)-

HRID 502622Notes

Reaction equation

HRID 502622 reaction equation
[O-:1]CC.[Mg+2].[O-]CC.[Mg].[CH3:9][C:10](=[O:15])[CH2:11][CH2:12][CH:13]=O.[N+:16]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])([O-:18])=[O:17].Cl>C1(C)C=CC=CC=1.C(O)C>[N+:16]([C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([CH:11]([C:10](=[O:15])[CH3:9])[C:12](=[O:1])[CH3:13])=[O:22])([O-:18])=[O:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 118752-Nitrobenzoyl chlorideHCID 164702Pentanal, 4-oxo-HCID 164963Magnesium ethanolateHCID 5462224Magnesium

Product 1

HCID 51248932,4-Pentanedione, 3-(2-nitrobenzoyl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Magnesium ethoxide was generated by refluxing ethanol (50 mL) with 1.2 g (50 mmol) Magnesium turnings for 3 days. The ethanol was removed under reduced 10 pressure, and 50 mL of toluene was added, followed by dropwise addition of 5 g (50 mmol) of 2,5-pentanedione. The reaction mixture was stirred at room temperature for two hours and then at 70° C. for one hour, and then cooled to −10° C. A solution of 9.27 g (50 mmol) of 2-nitrobenzoyl chloride in 20 mL of toluene was added dropwise, and the solution was stirred at ambient temperature for 18 hours. The reaction mixture was 15 poured into a mixture of ice and 1N HCl, and the resulting solution was extracted with ethyl acetate. The organic layert was washed with brine, dried (MgSO4) filtered and concentrated to dryness under reduced pressure to afford 12.23 g of 3-(2-nitro-benzoyl)-pentane-2,4-dione

Workup

  1. customThe ethanol was removed
  2. additionwas added
  3. waitat 70° C. for one hour
  4. temperaturecooled to −10° C
  5. stirringthe solution was stirred at ambient temperature for 18 hours
  6. extractionthe resulting solution was extracted with ethyl acetate
  7. washThe organic layert was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-be7c507f3f6445fc9c62e91db301e43b
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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