Hydrochloric Acid → 3,4,5-Trimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene

HRID 1885764Notes

Reaction equation

HRID 1885764 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7](OC)[C:6]=1[O:16][CH3:17].C1C=CC=CC=1.[CH3:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].Cl.[O:32]1CCC[CH2:33]1>CCCCCC>[CH3:33][O:32][C:13]1[CH:12]=[C:8]([C:9](=[O:11])[CH2:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:7]=[C:6]([O:16][CH3:17])[C:5]=1[O:4][CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86746137Benzene trimethoxybenzoate

Product 1

HCID 197775673,4,5-Trimethoxy(4,4-dimethyl-3-oxopentanoyl)benzeneYield 74%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 3.0 gm (75 mmol) of 60% sodium hydride, 10 gm (44.3 mmol) of methyl 3,4,5-oxopentanoyl)benzene trimethoxybenzoate, and 80 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 5.3 gm (53.2 mmol) of pinacolone was added dropwise. Refluxing under heat was continued for 5 hours. After cooling the reaction mixture, 45 ml of 2N hydrochloric acid was added, the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 9.6 gm of the target compound as colorless needles (yield: 74%).

Workup

  1. customIn a 200 ml three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and a nitogen-inlet tube
  3. temperaturerefluxed
  4. additionwas added dropwise
  5. temperatureRefluxing
  6. temperatureunder heat
  7. additionwas added
  8. extractionthe mixture was extracted twice with chloroform
  9. dry with materialThe extract was dried over anhydrous sodium sulfate
  10. customthe solvent was removed by evaporation
  11. customto give a crude product
  12. filtrationwere filtered off
  13. concentrationThe filtrate was concentrated by evaporation, and recrystallization

Sources & evidence

ORD record
ord-1141df1a547744d5b9fc9662a70f682a
Source dataset
uspto-grants-1992_09
Patent number
US05146002

Reaction notes

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