Acetyl chloride → (1R)-Camphoric anhydride

HRID 1358591

Reaction equation

HRID 1358591 reaction equation
[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]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 101807Camphoric Acid

Product 1

HCID 68989(1R)-Camphoric anhydride

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f039574d2a6545d794080ffa6e528d48
Source dataset
uspto-grants-2003_07
Patent number
US06596752B1

Linked notes

Loading…