Thionyl Chloride → (R)-(-)-chlorobutyric acid ethyl ester

HRID 2351837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351837
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C@@H:6](O)[CH3:7])[CH3:2].O=S(Cl)[Cl:12]>C1C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[CH2:1]([O:3][C:4](=[O:9])[C@H:5]([Cl:12])[CH2:6][CH3:7])[CH3:2]

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 6950306Butanoic acid, 3-hydroxy-, ethyl ester, (3S)-

Produkt 1

HCID 86743449(R)-(-)-chlorobutyric acid ethyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

0.24 moles (S)-(+)-3-hydroxy-butyric acid ethyl ester in 100 ml benzene are added to 0.07 moles anhydrous ZnCl2 while agitating and while excluding moisture. Subsequently, 0.72 moles SOCl2 are added, and the product is agitated at room temperature for two days. Then the reaction mixture is treated with saturated NaHClO3 solution. After separating off the aqueous phase, it is dried with Na2SO4. The solvent is distilled off, and the residue is fractionally distilled. One obtains (R)-(-)-chlorobutyric acid ethyl ester with a yield of 65 percent.

Aufarbeitung

  1. stirringthe product is agitated at room temperature for two days
  2. customAfter separating off the aqueous phase, it
  3. dry with materialis dried with Na2SO4
  4. distillationThe solvent is distilled off
  5. distillationthe residue is fractionally distilled

Quellen und Nachweise

ORD-Eintrag
ord-4c0baf93b43541549fa78343c2063a4d
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04874544

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