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

HRID 1018160

反応式

HRID 1018160 の反応式
[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]

参加物

6

反応物 2

HCID 8842CitronellolHCID 5386474-Oxo capric acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 3283Diethyl Ether溶媒HCID 8078Cyclohexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-11630feaa8de4c1b838b6cbecb81d087
出典データセット
uspto-grants-2002_11
特許番号
US06479682B1

関連ノート

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