Hydrochloric Acid → 1-(3-Dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione

HRID 1613013Notes

Reaction equation

HRID 1613013 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:16])[C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10]CC)=O.[CH3:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].Cl>O1CCCC1>[CH3:16][N:4]([CH3:3])[C:5]1[CH:6]=[C:7]([C:8](=[O:10])[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 24758Sodium hydrideHCID 12833325Ethyl 3-(dimethylamino)benzoate

Product 1

HCID 189544861-(3-Dimethylaminophenyl)-4,4-dimethylpentane-1,3-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube, were charged 2.08 gm (31 mmol) of 60% sodium hydride and 5.0 gm (26 mmol) of ethyl 3-dimethylaminobenzoate. The mixture was dispersed in 40 ml of tetrahydrofuran and heated under refluxing. To the mixture was dropwise added 3.0 gm (30 mmol) of pinacolone and the mixture was heated with stirring for 3 hours. After cooling, 50 ml of 1N hydrochloric acid was added to the reaction mixture, and the organic layer was extracted twice with chloroform. The extract was thoroughly washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain an yellow oil. The oily substance was submitted to the Kugelrohr distillation at 200° C., 1 mmHg, and crystallized from hexane to give 4.81 gm (yield: 75%) of yellow solid product.

Workup

  1. customInto a 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube
  2. temperatureheated
  3. temperatureunder refluxing
  4. temperaturethe mixture was heated
  5. temperatureAfter cooling
  6. extractionthe organic layer was extracted twice with chloroform
  7. washThe extract was thoroughly washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by evaporation
  10. customto obtain an yellow oil
  11. distillationThe oily substance was submitted to the Kugelrohr distillation at 200° C.
  12. custom1 mmHg, and crystallized from hexane

Sources & evidence

ORD record
ord-7172cb5f5ef1430b98bd0c07da73f24d
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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