Acetone → 4'-(3-Phenylpropoxy)acetophenone

HRID 461023Notes

Reaction equation

HRID 461023 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:11]1([CH2:17][CH2:18][CH2:19]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[C:11]1([CH2:17][CH2:18][CH2:19][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzene

Product 1

HCID 195962364'-(3-Phenylpropoxy)acetophenoneYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 68.1 g (0.5 mole) of 4'-hydroxyacetophenone, 100.3 g (0.5 mole) of a 3-phenylpropyl bromide, 69.0 g (0.5 mole) of potassium carbonate and 500 ml of anhydrous acetone is refluxed with stirring for 8 hours. After adding 1 liter of water the product is extracted into ether, the extract is washed with water and 2 N sodium carbonate solution and dried over anhydrous sodium sulfate and the solvent is evaporated. The resulting oil (125.8 g) begins to crystallize and yields after two recrystallizations from ether-hexane and ether, respectively, 73.9 g (58% yield) of the desired product, M.P. 80°-81°.

Workup

  1. temperatureis refluxed
  2. extractionis extracted into ether
  3. washthe extract is washed with water and 2 N sodium carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is evaporated
  6. customto crystallize
  7. customyields
  8. customafter two recrystallizations from ether-hexane and ether

Sources & evidence

ORD record
ord-7e5ca07aecdf49eaa311c4f51fa463b4
Source dataset
uspto-grants-1977_12
Patent number
US04061746

Reaction notes

Loading…