Hydrochloric Acid → 4-Cyano-3-hydroxybutanoic acid

HRID 1816193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816193
[Cl-].[Ca+2].[Cl-].[OH-].[Ca+2].[OH-].Br[CH2:8][CH:9]([OH:15])[CH2:10][C:11]([O:13]C)=[O:12].[C-:16]#[N:17].[Na+].Cl>O.C(OCC)(=O)C>[C:16]([CH2:8][CH:9]([OH:15])[CH2:10][C:11]([OH:13])=[O:12])#[N:17]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 5284359Calcium ChlorideHCID 6093208Calcium HydroxideHCID 9855736Methyl 4-bromo-3-hydroxybutanoate

Produkt 1

HCID 98988294-Cyano-3-hydroxybutanoic acidAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.6 g of calcium chloride (15 mmol) and 0.6 g (8.1 mmol) of calcium hydroxide were dissolved in 3.7 ml of water and stirred at room temperature for 20 minutes. At the same temperature, 2.00 g (10 mmol) of methyl 4-bromo-3-hydroxybutanoate was added dropwise over 5 minutes. After stirring for further ten minutes, the mixture was cooled by ice, and 0.6 g (12 mmol) of sodium cyanide was added thereto. Then, the mixture was stirred at an internal temperature of 25 to 33° C. for 4.5 hours. Then, concentrated hydrochloric acid was added dropwise in the reaction solution, and ethyl acetate was used for extraction five times. The organic layer was concentrated under reduced pressure to get 1.2 g of 4-cyano-3-hydroxybutanoic acid. The purity of the obtained 4-cyano-3-hydroxybutanoic acid was 91% (high-performance liquid chromatography in area percentage).

Aufarbeitung

  1. stirringAfter stirring for further ten minutes
  2. additionwas added
  3. stirringThen, the mixture was stirred at an internal temperature of 25 to 33° C. for 4.5 hours
  4. extractionwas used for extraction five times
  5. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eb99fd47f79b4199bd98df015ae173b5
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884607B2

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