Toluene → 2-(2-(Diallylamino)-2-oxoethyl)dec-3-enoic acid

HRID 907248

Reaktionsgleichung

Reaktionsgleichung von HRID 907248
[CH:1]([CH:13]1[CH2:18][C:17](=[O:19])[O:16][C:14]1=[O:15])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]CCCC.[CH2:20]([NH:23][CH2:24][CH:25]=[CH2:26])[CH:21]=[CH2:22].C1(C)C=CC=CC=1>O>[CH2:20]([N:23]([CH2:24][CH:25]=[CH2:26])[C:17](=[O:19])[CH2:18][CH:13]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14]([OH:16])=[O:15])[CH:21]=[CH2:22]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 31279DiallylamineHCID 329333-(1-Dodecen-1-yl)dihydro-2,5-furandione

Produkt 1

HCID 725398112-(2-(Diallylamino)-2-oxoethyl)dec-3-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 500 ml, two-neck flask was charged with 105.2 g (500 mmol) dodecenylsuccinic anhydride 100 ml toluene. The flask was equipped with a thermometer and immersed in a water bath. Diallylamine (48.6 g, 500 mmol) was then dripped into the magnetically stirred anhydride plus toluene solution over a 15-minute period. Ice was added to the water bath as required to prevent temperature of the reaction mixture from getting above 35° C. The mixture was then stirred for another 45 minutes at room temperature. The toluene was then removed via rotary evaporator and air sparge to yield 153.4 g (99.8% of theory) of a red, oily liquid. An FTIR trace on this compound was found to have significant absorptions at 2924, 1726, 1605, 1440, 1221, 1174, 972, and 922 wavenumbers.

Aufarbeitung

  1. customThe flask was equipped with a thermometer
  2. customimmersed in a water bath
  3. customfrom getting above 35° C
  4. customThe toluene was then removed via rotary evaporator and air
  5. customsparge
  6. customto yield 153.4 g (99.8% of theory) of a red, oily liquid

Quellen und Nachweise

ORD-Eintrag
ord-4bc8e31505e944be9fafcab72211fea9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013104B2

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