Acetyl chloride → (1R)-Camphoric anhydride

HRID 1358591

Reaktionsgleichung

Reaktionsgleichung von HRID 1358591
[C:1]([OH:14])(=[O:13])[C@@:2]1([CH2:12][CH2:11][C@H:7]([C:8]([OH:10])=O)[C:4]1([CH3:6])[CH3:5])[CH3:3].C(Cl)(C)=O.CC(OC(C)=O)=O>>[C:1]1(=[O:13])[O:14][C:8](=[O:10])[CH:7]2[CH2:11][CH2:12][C@@:2]1([C:4]2([CH3:5])[CH3:6])[CH3:3]

Komponenten

4

Edukt 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 101807Camphoric Acid

Produkt 1

HCID 68989(1R)-Camphoric anhydride

Versuchsvorschrift

A mixture of (1R-cis)-1,2,2-Trimethylcyclopentane-1,3-dicarboxylic acid) [(1R,3S)-camphoric acid] (40.0 g), AcCl (23.5 g), and Ac2O (81.6 g) was heated under reflux for 3 hr. The mixture was concentrated in vacuo, dissolved in CHCl3, washed with sat. NaHCO3, brine, and dried over Na2SO4. The solvent was removed in vacuo and the residue was triturated with i-Pr2O to give (1R)-1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione [(1R)-camphoric anhydride (34.0 g) as crystals.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutiondissolved in CHCl3
  5. washwashed with sat. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was triturated with i-Pr2O

Quellen und Nachweise

ORD-Eintrag
ord-f039574d2a6545d794080ffa6e528d48
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596752B1

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