Water → HCID 890054, compound

HRID 1641521Notes

Reaction equation

HRID 1641521 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].[Cl-].[NH4+].C(OCC)(=O)C>[CH2:18]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 701334-Hydroxy-2-methylacetophenone

Product 1

HCID 890054HCID 890054, compoundYield 105.1%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 4′-hydroxy-2′-methylacetophenone (3.06 g, 20 mmol) in N,N-dimethylformamide (20 mL), potassium carbonate (3.66 g, 26.4 mmol), benzyl bromide (2.7 mL, 22.4 mmol) and n-Bu4NI (0.75 g, 2.03 mmol) were added and stirred at room temperature for 14 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride under ice cooling, followed by addition of water and ethyl acetate to separate the organic layer. The organic layer was washed with 20 wt. % aqueous sodium thiosulfate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1→6:1) to give the titled compound (5.05 g, quant.) as a colorless powder.

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with 20 wt. % aqueous sodium thiosulfate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtering off the desiccant
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1→6:1)

Sources & evidence

ORD record
ord-137f5ae211c04dc58a94abbacebec4a3
Source dataset
uspto-grants-2012_02
Patent number
US08115017B2

Reaction notes

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