4'-Hydroxypropiophenone → 1-[4-(3-Chloropropoxy)phenyl]-1-propanone

HRID 1709846Notes

Reaction equation

HRID 1709846 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62714'-HydroxypropiophenoneHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 123996851-[4-(3-Chloropropoxy)phenyl]-1-propanoneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 37.6 g (0.25 mole) of 4'-hydroxypropiophenone (97%)*, 78.7 g (0.5 mole) of 1-bromo-3-chloropropane and 103.5 g (0.75 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 18 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure. The oily residue was dissolved in 500 ml of benzene and the solution stirred with potassium hydroxide pellets for 1.5 hr to remove unreacted phenol. The mixture was filtered and the filtrate was concentrated to give 56.1 g (99% yield) of title compound as an oil. The oil gradually crystallized and a portion of the solid was recrystallized from petroleum ether (60°-110° C.) to yield title compound as a fluffy, white solid, mp 41°-43° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionThe oily residue was dissolved in 500 ml of benzene
  7. customto remove unreacted phenol
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f163206c0d504c48a0384fa0ae3200b0
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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