Potassium Carbonate → 1-(2-(Cyclopropylmethoxy)-6-(4-methoxybenzyloxy)phenyl)ethanone

HRID 2115644Notes

Reaction equation

HRID 2115644 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:7]=2[C:13](=[O:15])[CH3:14])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[C:7]=2[C:13](=[O:15])[CH3:14])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 222587731-(2-(Cyclopropylmethoxy)-6-hydroxyphenyl)ethanone

Product 1

HCID 99233791-(2-(Cyclopropylmethoxy)-6-(4-methoxybenzyloxy)phenyl)ethanoneYield 89.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-{2-[(cyclopropylmethyl)oxy]-6-hydroxyphenyl}ethanone (56.3 g, 272 mmol) in acetone (1000 mL) was added potassium carbonate (188 g, 1364 mmol), 4-methoxybenzyl chloride (40.9 mL, 300 mmol) and tetrabutylammonium iodide (20.2 g, 54.6 mmol). The mixture was stirred at reflux overnight. The reaction mixture was allowed to cool to room temperature, filtered on Celite®, and then the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Then the resulting white solid was recrystallized from ethanol, collected by filtration, washed with ethanol, and dried under reduced pressure to give 1-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}ethanone as a white solid (79.2 g, yield; 89%).

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered on Celite®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe separated organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThen the resulting white solid was recrystallized from ethanol
  11. filtrationcollected by filtration
  12. washwashed with ethanol
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-5ad36c94514a41eda6b537dab2c37ab4
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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