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

HRID 482624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482624
[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]

Komponenten

5

Edukt 3

HCID 74694'-HydroxyacetophenoneHCID 14797Potassium HydroxideHCID 336431-Iodopropane

Produkt 1

HCID 2601321-(4-Propoxyphenyl)ethan-1-oneAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-50a629343a1b417f93f1b421554ebba0
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05798311

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