4'-Hydroxyacetophenone → HCID 3026312, compound

HRID 1690190Notes

Reaction equation

HRID 1690190 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), and the resultant mixture was sequentially added with tetrabutylammonium 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), and stirred at 70° C. overnight. The reaction solution was filtered, washed with acetone, and concentrated in vacuo. The resultant residue was added with 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 resultant residue was added with 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-eae8ae3986ad4a7785240d74604fdccf
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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