Hydrochloric Acid → HCID 14403266, compound

HRID 2291220Notes

Reaction equation

HRID 2291220 reaction equation
[C:1]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Mg+2].[O-]CC.[N+:20]([C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26])([O-:22])=[O:21].Cl>C(OCC)C>[C:10]([CH:9]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[C:25]([C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[N+:20]([O-:22])=[O:21])=[O:26])(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7166BenzoylacetoneHCID 118752-Nitrobenzoyl chlorideHCID 164963Magnesium ethanolate

Product 1

HCID 14403266HCID 14403266, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of benzoylacetone (8.1 g, 0.05 mole), magnesium ethoxide (5.7 g, 0.05 mole) and ethyl ether (100 ml) was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, and 2-nitrobenzoyl chloride (11.1 g, 0.06 mole) was added dropwise over a period of 15 minutes. The reaction mixture was then heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured into 50 ml of 2N hydrochloric acid, and the phases separated. The ether layer was extracted with 5% potassium carbonate. The basic extract was acidified with hydrochloric acid and extracted with ether. The ether extract was washed with saturated sodium chloride, dried over magnesium sulfate and concentrated under vacuum yielding 11.4 g of the desired product as a white solid with a melting point of 99°-103° C. It was identified as such by nuclear magneticresonance spectroscopy, infrared spectroscopy and mass spectroscopy.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for 1 hour
  5. temperatureAfter cooling to room temperature
  6. customthe phases separated
  7. extractionThe ether layer was extracted with 5% potassium carbonate
  8. extractionThe basic extract
  9. extractionextracted with ether
  10. extractionThe ether extract
  11. washwas washed with saturated sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-915cb3a9c0664bc58af3ccf1a2398e2c
Source dataset
uspto-grants-1989_01
Patent number
US04795489

Reaction notes

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