Reaktion #65011

Reaktionsgleichung

2,6-di-tertiary-butyl-p-benzoquinone

3-(4-aminophenyl)propionic acid

boron trifluoride etherate

→

3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid

Ausbeute 55.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated on a steam cone under a slow stream of nitrogen for two hours
2. 2
   SonstigeThe resulting solid was triturated with hexane
3. 3
   Sonstigecollected
4. 4
   Waschenrinsed with hexane
5. 5
   Sonstigerecrystallized from a mixture of ethyl acetate and hexane

Vorschrift

A mixture of 5.51 g (0.025 mole) of 2,6-di-tertiary-butyl-p-benzoquinone, 4.54 g (0.027 mole) of 3-(4-aminophenyl)propionic acid, 50 ml of tetrahydrofuran and 0.25 ml of boron trifluoride etherate was heated on a steam cone under a slow stream of nitrogen for two hours. The resulting solid was triturated with hexane, collected, rinsed with hexane and recrystallized from a mixture of ethyl acetate and hexane to give 5.1 g yellow 3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid, m.p. 165°-167° C. Analysis: Calculated for C23H29NO3 : % C, 75.2; % H, 8.0; % N, 3.8; Found % C, 74.8; % H, 7.9; % N, 3.7.

Quelle