Pyridine → 6,8-dichlorooctanoic Acid

HRID 2983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2983
[Cl:1][CH2:2][CH2:3][CH:4](O)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].N1C=CC=CC=1.S(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][CH:4]([CH2:3][CH2:2][Cl:1])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 109544588-Chloro-6-hydroxyoctanoic acid

Produkt 1

HCID 99644476,8-dichlorooctanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of 2.4 g (11.0 mmoles) of the methyl ester of (+)-8-chloro-6hydroxy-octanoic acid (+)-(VIII) (R=Me) and 0.04 g (0.5 mmoles) of pyridine in 8 ml toluene, 1.6 g (13.5 mmoles) of thionyl chloride in 5 ml of toluene were added slowly. The mixture was then refluxed for 1 hour. After cooling to room temperature, the reaction mixture was added to 20 ml ice water and the organic phase was separated and washed with 10 mL of water and dried over magnesium sulfate. After that, the solvent was evaporated under vacuum. The methyl ester of (-)-6,8-Dichloro-octanoic acid (-)-(III), (R=Me) was obtained in a yield of 2.0 g (81% of the theoretical yield). [α]D20 =-30.0° (c=1, benzene).

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 1 hour
  2. customthe organic phase was separated
  3. washwashed with 10 mL of water
  4. dry with materialdried over magnesium sulfate
  5. customAfter that, the solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ad0e6003b3be4ab6ac0a6c1f57d6ff26
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731448

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