Water → ethyl (E,E)-4-ethyl-2,4-hexadienoate

HRID 1656801

Reaktionsgleichung

Reaktionsgleichung von HRID 1656801
C[O-].[Na+].C(OP([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(OCC)=O)C.[CH2:18](/[C:20](=[CH:23]\[CH3:24])/[CH:21]=O)[CH3:19].O>CO.C1(C)C=CC=CC=1>[CH2:23](/[C:20](=[CH:18]\[CH3:19])/[CH:21]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:24]

Komponenten

7

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 53628972-Butenal, 2-ethyl-HCID 10942334Sodium Methoxide

Produkt 1

HCID 10899087ethyl (E,E)-4-ethyl-2,4-hexadienoateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 12.7 kg (235 mol) of sodium methoxide and 48.0 kg (214 mol) of ethyl diethylphosphonoacetate in 40 l of methanol is added dropwise 20 kg (204 mol) of 2-ethylcrotonaldehyde at 20°-30° C. during 0.5 hour. After stirring for 2 hours at same temperature, the reaction mixture is poured into the solution of 180 l of water and 120 l of toluene. The toluene layer is separated and combined with 50 l toluene extract of aqueous phase, and washed with two 120 l portions of saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent is removed and the residue is distilled under reduced pressure to give ethyl (E,E)-4-ethyl-2,4-hexadienoate (Yield 28.5 kg) (83.1%), b.p. 41°-75° C./5-8 mmHg.

Aufarbeitung

  1. customThe toluene layer is separated
  2. extractionextract of aqueous phase
  3. washwashed with two 120 l portions of saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent is removed
  6. distillationthe residue is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8fb2cd8877ca4f1298b0858e710b428e
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05254733

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