Camphene → exo-3,3-Dimethylbicyclo(2.2.1)heptane-2-propionic acid

HRID 1390550

反応式

HRID 1390550 の反応式
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.[CH:8]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[C:12](=[CH2:13])[C:9]2([CH3:11])[CH3:10].C(OOC(C)(C)C)(C)(C)C.[OH-].[Na+]>>[CH3:10][C:9]1([CH3:11])[CH:8]2[CH2:17][CH:14]([CH2:15][CH2:16]2)[CH:12]1[CH2:13][CH2:6][C:5]([OH:4])=[O:7]

参加物

5

反応物 4

HCID 6616CampheneHCID 7918Acetic AnhydrideHCID 8033Di-tert-butyl peroxideHCID 14798Sodium Hydroxide

生成物 1

HCID 6455393exo-3,3-Dimethylbicyclo(2.2.1)heptane-2-propionic acid

実験手順

To refluxing acetic anhydride (1050 g., 10 moles), there is added dropwise over six hours a solution of camphene (136 g., 1 mole) and di-tert-butyl peroxide (0.1 mole, 14.6 g.). After complete addition, the mixture is heated at reflux for five hours. The cooled reaction mixture is concentrated under reduced pressure to leave a yellow-orange residual oil, 750 ml. of 2.5N NaOH is added to the residue which is then heated on the steam bath for one hour. The cooled solution is extracted once with ether, made acidic with concentrated HCl, and extracted thoroughly with ether. The dried (Na2SO4) ether extracts are concentrated under reduced pressure and the residue distilled under vacuum.

後処理

  1. additionAfter complete addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for five hours
  4. customThe cooled reaction mixture
  5. concentrationis concentrated under reduced pressure
  6. customto leave a yellow-orange residual oil, 750 ml
  7. temperatureis then heated on the steam bath for one hour
  8. extractionThe cooled solution is extracted once with ether
  9. extractionextracted thoroughly with ether
  10. dry with materialThe dried (Na2SO4) ether extracts
  11. concentrationare concentrated under reduced pressure
  12. distillationthe residue distilled under vacuum

出典と根拠

ORDレコード
ord-00737a1b7cbd4f5b838dec7cf12cd5bb
出典データセット
uspto-grants-1979_02
特許番号
US04139559

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