Sulfuric Acid → 3-(2,4-Dichlorobenzoyl)pentane-2,4-dione

HRID 1251963Notes

Reaction equation

HRID 1251963 reaction equation
[O-:1][CH2:2][CH3:3].[Mg+2].[O-:5][CH2:6][CH3:7].[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12].S(=O)(=O)(O)O.[CH3:24]COCC>>[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([CH:3]([C:6](=[O:5])[CH3:7])[C:2](=[O:1])[CH3:24])=[O:12]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 666452,4-Dichlorobenzoyl chlorideHCID 164963Magnesium ethanolate

Product 1

HCID 141532833-(2,4-Dichlorobenzoyl)pentane-2,4-dione

Procedure

A mixture of magnesium ethoxide (22.9 g, 0.2 moles) 2,4-pentanedione (20.0 g, 0.2 moles), and ether (150 ml) was heated at reflux for 1 hour. 2,4-Dichlorobenzoyl chloride (41.9 g, 0.2 mole) in ether (50 ml) was added to the mixture over a period of 15 minutes, and the resultant mixture was heated at reflux for an additional 0.5 hour. After cooling, the reaction mixture was poured into 200 ml of 10% sulfuric acid. The ether layer was separated and stirred with 250 ml of 5% copper (II) acetate. The resulting copper salt was filtered, washed with ether, and stirred with 6N hydrochloric acid to destroy the salt. The acidic aqueous solution was extracted with ether. The ether extract was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under vacuum yielding 21 g of the desired product as a yellow oil. It was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectroscopy.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureat reflux for an additional 0.5 hour
  4. temperatureAfter cooling
  5. customThe ether layer was separated
  6. filtrationThe resulting copper salt was filtered
  7. washwashed with ether
  8. stirringstirred with 6N hydrochloric acid
  9. customto destroy the salt
  10. extractionThe acidic aqueous solution was extracted with ether
  11. extractionThe ether extract
  12. washwas washed with saturated sodium chloride
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2479c9b791c1431f9fc527ffd40080cb
Source dataset
uspto-grants-1988_05
Patent number
US04741769

Reaction notes

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