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

HRID 1613005Notes

Reaction equation

HRID 1613005 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=O.[CH3:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].Cl>CCCCCC.O1CCCC1>[CH3:18][O:17][C:13]1[CH:12]=[C:7]([C:8](=[O:10])[CH2:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH:6]=[C:5]([O:4][CH3:3])[C:14]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 15956Methyl 3,4,5-trimethoxybenzoateHCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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-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-af23f4b663924bea9becb7e5ce01a7ac
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

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