6-Chloro-1-hexanol → (E)-4-butoxy-3-methoxycinnamic acid 6-hydroxyhexyl ester

HRID 2307523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307523
[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:8][C:7]=1[O:17][CH3:18])[CH2:2][CH2:3][CH3:4].Cl[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]1[CH:15]=[CH:16][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[C:7]([O:17][CH3:18])[CH:8]=1

Komponenten

5

Edukt 2

HCID 748286-Chloro-1-hexanolHCID 59335643-(4-Butoxy-3-methoxyphenyl)prop-2-enoic acid

Produkt 1

HCID 20744698(E)-4-butoxy-3-methoxycinnamic acid 6-hydroxyhexyl esterAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

1.38 g (5.50 mmol) (E)-4-butyloxy-3-methoxycinnamic acid was suspended in 3 ml acetonitrile. A mixture of 0.84 g (5.50 mmol) 1,8-diazabicyclo[5 4.0]undec-7-ene(1,5-5) (DBU) and 3 ml acetonitrile was added dropwise over a period of 5 minutes. 0.46 g (1.25 mmol) tetrabutylammonium iodide and 0.68 g (5.00 mmol) 6-chlorohexanol was added and the resulting mixture was then refluxed for 6 hours. The reaction mixture was cooled and then extracted using ethyl acetate and water. The ethyl acetate phase was washed with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography using a silica gel column (120 g) and toluene:ethyl acetate (1:1) as eluant to give 1.39 g (79%) (E)-4-butyloxy-3-methoxycinnamic acid 6-hydroxyhexyl ester as colourless oil.

Aufarbeitung

  1. additionwas added dropwise over a period of 5 minutes
  2. temperaturethe resulting mixture was then refluxed for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted
  5. washThe ethyl acetate phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-96b0c7a0bfa341cf9e930b6e154179d3
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831148B2

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