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Propionic Acid → methyl (4E)-octa-4,7-dienoate

HRID 356571
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 356571
[C:1](OC)([O:5][CH3:6])([O:3]C)[CH3:2].C(O)(=O)CC.[CH2:14]=[CH:15][CH:16](O)[CH2:17][CH:18]=[CH2:19]>COC(C)(C)C>[C:1]([O:5][CH3:6])(=[O:3])[CH2:2][CH2:14]/[CH:15]=[CH:16]/[CH2:17][CH:18]=[CH2:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1032Propionic AcidHCID 15050Trimethyl orthoacetateHCID 791221,5-Hexadien-3-ol

Produkt 1

HCID 10986465methyl (4E)-octa-4,7-dienoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

78.0 g (about 0.71 mol) of 1,5-hexadien-3-ol, obtained by a Grignard reaction from allylmagnesium bromide and acrolein, were dissolved in 198.0 g (1.65 mol) of trimethyl orthoacetate and 3.0 g (0.04 mol) of propionic acid were then added. The reaction mixture was heated to 120° C. and the methanol formed during the reaction was distilled off over a 15 cm Widmer column. After 2 hours, the reaction mixture was held at 130° C. for a further 1 hour to complete the reaction and was then cooled to room temperature, diluted with 500 ml of tert-butyl methyl ether and the solution was washed twice with 100 ml of saturated sodium bicarbonate solution, dried with sodium sulphate and concentrated. Distillation of the resulting 128 g of crude product over a 20 cm Widmer column gave 51.6 g of olfactorily good methyl (E)-4,7-octadienoate of boiling point 76° C./17 mbar and with a purity of about 98%.

Aufarbeitung

  1. distillationwas distilled off over a 15 cm Widmer column
  2. waitthe reaction mixture was held at 130° C. for a further 1 hour
  3. customthe reaction
  4. temperaturewas then cooled to room temperature
  5. washthe solution was washed twice with 100 ml of saturated sodium bicarbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. distillationDistillation of the resulting 128 g of crude product over a 20 cm Widmer column

Quellen und Nachweise

ORD-Eintrag
ord-d21c18e4298344ca912e75272cdd9aaf
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05837671

Notizen zur Reaktion

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