Ethanol → Phytanic Acid

HRID 2228415

반응식

HRID 2228415 반응식
[CH2:1]([OH:21])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4].C([OH:24])C>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([OH:24])(=[O:21])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4]

참가 물질

6

반응물 2

HCID 702EthanolHCID 102459Dihydrophytol

생성물 1

HCID 26840Phytanic Acid

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

Phytanol (19.5 g) was dissolved in acetic acid (250 ml) and cooled in an ice bath. Chromium trioxide (21.0 g) dissolved in a minimum amount of water was added to the above solution and stirred at room temperature for 18 hours. Ethanol (50 ml) was slowly added to the reaction mixture and stirred for a further 3 hours. Most of solvent was removed and water (250 ml) was added. This solution was extracted with ether (2×200 ml) and the combined ether extract was dried (MgSO4), decolourized with activated charcoal and filtered through a thin flash silica bed. The solvent was removed and the crude product chromatographed on flash silica (1-4% methanol in dichloromethane) to give phytanoic acid as a pale yellow liquid. Yield 7.03 g, 34%.

후처리

  1. temperaturecooled in an ice bath
  2. additionwas added to the above solution
  3. stirringstirred for a further 3 hours
  4. customMost of solvent was removed
  5. additionwater (250 ml) was added
  6. extractionThis solution was extracted with ether (2×200 ml)
  7. extractionthe combined ether extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered through a thin flash silica bed
  10. customThe solvent was removed
  11. customthe crude product chromatographed on flash silica (1-4% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-315bc8f445844245b769925f7b627d87
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417009B1

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