Acetic Acid → 2-(4-Hexylphenyl)acetic acid

HRID 244932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244932
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10](C(=O)C)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:16]([OH:19])(=[O:18])[CH3:17].S(=O)(=O)(O)O>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([CH2:17][C:16]([OH:19])=[O:18])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 1234624-Hexylacetophenone

Produkt 1

HCID 20634302-(4-Hexylphenyl)acetic acidAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

12.0 g (39.3 mmol) of 1-(4-hexylphenyl)ethanone was dissolved in 23.6 g (393 mmol) of glacial acetic acid, mixed with 4.95 g (275 mmol) of water and 5.79 g (58.9 mmol) of sulfuric acid and heated at 150° C. for 6.5 hours under reflux. After completion of the reaction, the reaction solution was diluted with 400 mL of water and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (1:20 to 1:4) as the eluent to give 5.74 g of the desired product as white crystals.

Aufarbeitung

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8a81c55930c345c4a60472693af08425
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658686B2

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