Ethanol → 3,7,11-Trimethyldodeca-2,4-dienoic acid

HRID 1576589노트

반응식

HRID 1576589 반응식
C(O)C.[OH-].[Na+].[CH3:6][C:7]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:8][C:9]([O:11]CC)=[O:10]>O>[CH3:6][C:7]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:8][C:9]([OH:11])=[O:10]

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 38759Ethyl 3,7,11-trimethyldodeca-2,4-dienoate

생성물 1

HCID 1037233,7,11-Trimethyldodeca-2,4-dienoic acid수율 58%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 350 ml. of ethanol, 105 ml. of water and 70 ml. of 50% aqueous sodium hydroxide is added 46.5 g. of ethyl 3,7,11-trimethyldodeca-2,4-dienoate (40% cis, trans and 60% trans, trans). The mixture is refluxed for about 19 hours. After cooling, ethanol is removed under reduced pressure and water added followed by extraction with ether to yield 3,7,11-trimethyldodeca-2,4-dienoic acid containing about 58% trans, trans isomer. Conversion of the thus-obtained acid to the S-benzyl-isothiouronium salt recrystallized from aqueous methanol, and regeneration of the acid with ether-aqueous hydrochloric acid provides crystalline trans, trans, 3,7,11-trimethyldodeca-2,4-dienoic acid.

후처리

  1. temperatureThe mixture is refluxed for about 19 hours
  2. temperatureAfter cooling
  3. customethanol is removed under reduced pressure and water
  4. additionadded
  5. extractionfollowed by extraction with ether

출처 및 근거

ORD 기록
ord-4cc709b6430f44c5affb161ef85850a1
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03981922

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