Sulfuric Acid → HCID 20662006, compound

HRID 1066706Notes

Reaction equation

HRID 1066706 reaction equation
[C:1]([O:5]C(=O)CC(C)=O)(C)([CH3:3])[CH3:2].CC[O-].CC[O-].[Mg+2].[CH3:19][C:20]1[C:21]([N+:30]([O-:32])=[O:31])=[C:22]([C:26]([CH3:29])=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].S(=O)(=O)(O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:19][C:20]1[C:21]([N+:30]([O-:32])=[O:31])=[C:22]([C:26]([CH3:29])=[CH:27][CH:28]=1)[C:23]([CH2:2][C:1](=[O:5])[CH3:3])=[O:24]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6101p-Toluenesulfonic acidHCID 15538Tert-butyl acetoacetateHCID 164963Magnesium ethanolateHCID 21195520HCID 21195520, compound

Product 1

HCID 20662006HCID 20662006, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

Then, acetoacetate t-butyl ester in an amount of 8.9 g (56 mmol) was added into 80 ml toluene solution containing magnesium ethylate in an amount of 6.4 g (56 mmol) and the resulting mixture was stirred for 2 hours at 80° C., cooled down to an ambient temperature and added dropwise with 15 ml toluene solution of 3,6-dimethyl-2-nitrobenzoyl chloride in an amount of 10.3 g. The obtained mixture was stirred for 2 hours under heating and reflux, added with 10% sulfuric acid and extracted with ethyl acetate. The resulting organic solvent layer was washed with water and dried with anhydrous magnesium sulfate, and the solvent therein was distillated out under reduced pressure. The residue obtained was dissolved in 100 ml benzene and added with p-toluene sulfonic acid in an amount of 4.9 g (26 mmol), and the mixture was stirred for 2 hours under heating and reflux. Then, the reacted solution was washed with water and dried with anhydrous magnesium sulfate, and the solvent in the reacted solution was distillated out under reduced pressure. The residue obtained was purified by means of silica gei column chromatography to obtain 3,6-dimethyl-2-nitrobenzoylacetone in an amount of 3.9 g.

Workup

  1. temperaturecooled down to an ambient temperature
  2. stirringThe obtained mixture was stirred for 2 hours
  3. temperatureunder heating
  4. temperaturereflux
  5. extractionextracted with ethyl acetate
  6. washThe resulting organic solvent layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe residue obtained
  9. stirringthe mixture was stirred for 2 hours
  10. temperatureunder heating
  11. temperaturereflux
  12. washThen, the reacted solution was washed with water
  13. dry with materialdried with anhydrous magnesium sulfate
  14. customThe residue obtained
  15. customwas purified by means of silica gei column chromatography

Sources & evidence

ORD record
ord-402d5bec77b34452ab9032912ed50f9c
Source dataset
uspto-grants-2001_06
Patent number
US06245716B1

Reaction notes

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