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

HRID 482624Notes

Reaction equation

HRID 482624 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+].I[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 14797Potassium HydroxideHCID 336431-Iodopropane

Product 1

HCID 2601321-(4-Propoxyphenyl)ethan-1-oneYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 500 g (3670 mmole) of 4'-hydroxyacetophenone dissolved in 1000 ml of ethanol was added 450 g (3620 mmole) of 45% aqueous potassium hydroxide. To this mixture was added 650 g (3820 mmole) of 1-iodopropane. The resulting mixture was refluxed for 2 hours, cooled, concentrated in vacuo, and the resulting mixture was dissolved in 1000 ml of diethyl ether and 1000 ml of water. The organic layer was separated, washed with brine adjusted to pH 13 with aqueous sodium hydroxide, dried over anhydrous magnesium sulfate, concentrated in vacuo, and distilled yielding 640 g of the desired compound, bp 110° C. at 0.2 torr.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. dissolutionthe resulting mixture was dissolved in 1000 ml of diethyl ether
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationdistilled

Sources & evidence

ORD record
ord-50a629343a1b417f93f1b421554ebba0
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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