Hydrochloric Acid → 1-(3,4-Dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione

HRID 1613004Notes

Reaction equation

HRID 1613004 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=O.[CH3:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].Cl>CCCCCC.O1CCCC1>[CH3:3][O:4][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:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 16522Methyl 3,4-DimethoxybenzoateHCID 24758Sodium hydride

Product 1

HCID 113345631-(3,4-Dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedioneYield 66%

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 nitrogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and 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 8.9 gm of the target compound as colorless needles (yield: 65%).

Workup

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

Sources & evidence

ORD record
ord-851e347281c64b08b5e36e1ea776d444
Source dataset
uspto-grants-1993_03
Patent number
US05191121

Reaction notes

Loading…