4'-Hydroxyacetophenone → HCID 3026312, compound

HRID 1038563Notes

Reaction equation

HRID 1038563 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([CH3:21])=[CH2:20]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:20][C:19](=[CH2:18])[CH2:21][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 3026312HCID 3026312, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

1-(4-Hydroxyphenyl)ethanone (1.36 g, 10 mmol) was dissolved in acetone (50 mL), tetrabutyl ammonium iodide (370 mg, 1.0 mmol), potassium carbonate (2.76 g, 20 mmol) and 3-chloro-2-methyl-1-propene (1.5 mL, 15 mmol) were added sequentially, and the mixture was stirred at 70° C. overnight. The reaction solution was filtered, washed with acetone and concentrated in vacuo. The obtained residue was added water and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with 1N-aqueous solution of sodium hydroxide and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. 1-(4-(2-Methylallyloxy)phenyl)ethanone (1.71 g (yield 90%)) was obtained as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered
  2. washwashed with acetone
  3. concentrationconcentrated in vacuo
  4. additionThe obtained residue was added water and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 1N-aqueous solution of sodium hydroxide and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e78541b7ccdc458c877fa4e467a23986
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…