4'-Hydroxyacetophenone → 1-[4-(3-Chloropropoxy)phenyl]ethanone

HRID 2296737Notes

Reaction equation

HRID 2296737 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14][Cl:15].[OH-].[K+]>CO>[Cl:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide2×

Product 1

HCID 126856131-[4-(3-Chloropropoxy)phenyl]ethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of p-hydroxyacetophenone (106 g) and 1-bromo-3-chloropropane (309 mL) in methanol (800 mL) was treated with potassium hydroxide (65.5 g). The mixture was stirred at reflux temperature for 2 hours when an additional portion of potassium hydroxide (65.5 g) was added and the resulting mixture maintained at reflux temperature for 16 hours. The reaction was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and unreacted 1-bromo-3-chloropropane removed ia distillation. The residue was dissolved in ether (500 mL), washed with water (500 mL), dried over magnesium sulfate, filtered and evaporated to yield the title compound (147 g).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture maintained
  3. temperatureat reflux temperature for 16 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo and unreacted 1-bromo-3-chloropropane removed ia distillation
  6. dissolutionThe residue was dissolved in ether (500 mL)
  7. washwashed with water (500 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-cb051a47497e4c5c940fb0e3f59acb30
Source dataset
uspto-grants-2002_12
Patent number
US06489337B1

Reaction notes

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