Lithium Hydroxide → Bicyclo[3.2.1]octane-1,5-dicarboxylic acid

HRID 1408854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408854
C[O:2][C:3]([C:5]12[CH2:12][C:9]([C:13]([O:15]C)=[O:14])([CH2:10][CH2:11]1)[CH2:8][CH2:7][CH2:6]2)=[O:4].[OH-].[Li+]>O1CCCC1.O>[C:9]12([C:13]([OH:15])=[O:14])[CH2:12][C:5]([C:3]([OH:4])=[O:2])([CH2:11][CH2:10]1)[CH2:6][CH2:7][CH2:8]2

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 13633976Dimethyl bicyclo[3.2.1]octane-1,5-dicarboxylate

Produkt 1

HCID 18767672Bicyclo[3.2.1]octane-1,5-dicarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of bicyclo[3.2.1]octane-1,5-dicarboxylic acid dimethyl ester (crude 3.01 g from step 2) in tetrahydrofuran (100 mL) was treated with 1 M of lithium hydroxide in water (75 mL) and warmed at 70° C. for 6 hours. The reaction was concentrated under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The aqueous layer was collected and washed again with ethyl acetate. The aqueous layer was acidified with 1N HCl to pH 2, and then extracted with ethyl acetate. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and evaporated to afford 725 mg of white solid, which was used in the next step without further purification.

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was collected
  4. washwashed again with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-818bc899fc184facbf9007cc5f5917a1
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921370B2

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