Citronellol → 4-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

HRID 1018160

반응식

HRID 1018160 반응식
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23]O)[CH3:21])[CH3:16]>C1CCCCC1.CCOCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:21][CH:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])[CH2:22][CH2:23][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

6

반응물 2

HCID 8842CitronellolHCID 5386474-Oxo capric acid

생성물 1

HCID 538305424-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester수율 91%

시약·촉매·용매 3

HCID 6101p-Toluenesulfonic acid촉매HCID 3283Diethyl Ether용매HCID 8078Cyclohexane용매

실험 절차

A solution of 20.0 g 4-oxo-1-decanoic acid (Synthesis, 1987, 408), 16.8 g citronellol extra and 0.5 g p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed in a flask equipped with a Dean-Stark trap for 3 hours. Then the reaction mixture was cooled, diluted with ether, washed with saturated NaHCO3 and water. The organic phase was dried, filtered and evaporated to dryness. The resulting oil was purified by chromatography to yield 31.7 g of a yellow oil.

후처리

  1. customequipped with a Dean-Stark trap for 3 hours
  2. temperatureThen the reaction mixture was cooled
  3. washwashed with saturated NaHCO3 and water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting oil was purified by chromatography

출처 및 근거

ORD 기록
ord-11630feaa8de4c1b838b6cbecb81d087
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479682B1

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