Acetyl chloride → (1R)-Camphoric anhydride

HRID 1358591

反応式

HRID 1358591 の反応式
[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]

参加物

4

反応物 3

HCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 101807Camphoric Acid

生成物 1

HCID 68989(1R)-Camphoric anhydride

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f039574d2a6545d794080ffa6e528d48
出典データセット
uspto-grants-2003_07
特許番号
US06596752B1

関連ノート

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