Ethylene Glycol → Benzyl oximino-acetoacetate ethylene ketal

HRID 1834101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834101
O.[N:2](=[CH:4][C:5](=[O:17])[CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[OH:3].[CH2:18](O)[CH2:19][OH:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:19]1[O:20][C:5]([CH:4]=[N:2][OH:3])([CH2:6][C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[O:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 86734531HCID 86734531, Verbindung

Produkt 1

HCID 86734545Benzyl oximino-acetoacetate ethylene ketalAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In a two liter flask fitted with a Dean Stark water separator and a condenser were placed 186.5 g. (0.85 mole) of benzyl oximino-acetoacetate [1.1], 62 g. (1 mole) of ethylene glycol, 800 ml. of benzene (reagent grade) and 2 g. (10.5 mmole) of p-toluenesulfonic acid monohydrate. The reaction mixture was boiled at reflux until 15 ml. of water was removed (3 hours). The benzene solution was washed once with saturated sodium bicarbonate solution and once with brine. After drying over anhyrous sodium sulfate, the benzene solution was evaporated, leaving 212 g. (94% yield) of benzyl oximino-acetoacetate ethylene ketal [2.1] as a light yellow oil ! Its NMR spectrum was consistent with the assigned structure. Generally, the product was used as such in subsequent reactions but one of the isomers can be crystallized2 from toluene-petroleum either (b.p. 30°-60° C.); m.p. 52° C.

Aufarbeitung

  1. temperatureat reflux until 15 ml
  2. customof water was removed (3 hours)
  3. washThe benzene solution was washed once with saturated sodium bicarbonate solution and once with brine
  4. dry with materialAfter drying over anhyrous sodium sulfate
  5. customthe benzene solution was evaporated
  6. customleaving 212 g

Quellen und Nachweise

ORD-Eintrag
ord-ef2f15c9ac05405a8e419b314b422ec9
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04068078

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