4'-Hydroxyacetophenone → 1-(4-Propoxyphenyl)ethan-1-one

HRID 1031241Notes

Reaction equation

HRID 1031241 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:14][CH2:15][CH3:16]>C(O)C>[CH2:14]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 78401-BromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 2601321-(4-Propoxyphenyl)ethan-1-oneYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 272 g (2000 mmole) of 4'-hydroxyacetophenone dissolved in 800 ml of ethanol was added 249 g (2000 mmole) of 45% aqueous potassium hydroxide. After stirring for 5 minutes, 270 g (2200 mmole) of 1-bromopropane was added and the mixture was refluxed for 6 hours. After cooling, the precipitated potassium bromide was filtered off and washed with diethyl ether. The combined organic layers were concentrated in vacuo and then redissolved in 500 ml of diethyl ether. The resulting solution was washed with 1M aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo yielding 270 g of the expected product, an oil, bp 110° C. at 1 torr.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated potassium bromide was filtered off
  4. washwashed with diethyl ether
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. dissolutionredissolved in 500 ml of diethyl ether
  7. washThe resulting solution was washed with 1M aqueous sodium hydroxide solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a889dbb3558445cc98559e091e18752d
Source dataset
uspto-grants-1992_04
Patent number
US05109014

Reaction notes

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