1-Butanol → Butoxyacetic acid

HRID 637912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637912
[Na].Cl[CH2:3][C:4]([OH:6])=[O:5].O.[CH2:8]([OH:12])[CH2:9][CH2:10][CH3:11]>>[C:4]([OH:6])(=[O:5])[CH2:3][O:12][CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

5

Edukt 4

HCID 2631-Butanol2×HCID 300Chloroacetic AcidHCID 962WaterHCID 5360545Sodium2×

Produkt 1

HCID 41958Butoxyacetic acid

Versuchsvorschrift

Sodium metal (16 g) was added to 92.5 ml of butanol and heated at reflux under nitrogen. After the sodium had reacted, chloroacetic acid (32.9 g) in 40 ml of butanol was added dropwise and then heated at reflux for twenty hours. The mixture, upon cooling to room temperature, was added to 1300 ml of water and extracted four times with 250-ml portions of diethyl ether. The aqueous phase was acidified to about pH 2 with aqueous hydrochloric acid and again extracted four times with 250-ml portions of diethyl ether. The organic extracts were combined and dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation afforded the title compound as an oil. Structure assignment was supported by the proton nmr spectrum.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under nitrogen
  3. temperatureheated
  4. temperatureat reflux for twenty hours
  5. extractionextracted four times with 250-ml portions of diethyl ether
  6. extractionagain extracted four times with 250-ml portions of diethyl ether
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-13b6b0305cea4d63b2a3f425e29df58f
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04559337

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