Reaktion #1745630

Reaktionsgleichung

hydrogen

N-(2-octyl)-p-phenylenediamine

3-isopropoxypropionaldehyde

→

N-(3-isopropoxypropyl)-N'-(2-octyl)-p-phenylenediamine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 20 g
2. 2
   Filtrationfiltered through celite
3. 3
   SonstigeThe filtrate is evaporated in vacuo
4. 4
   workup.ADDITIONtreated with an excess of dry hydrogen chloride gas
5. 5
   FiltrationThe resulant solid is collected by filtration
6. 6
   Sonstigerecrystallized from methanol-acetone

Vorschrift

A mixture of 20 g. of N-(2-octyl)-p-phenylenediamine, 14 g. of 3-isopropoxypropionaldehyde and 0.3g. of 5% platinum sulfide on carbon catalyzt is shaken in a rocker bomb at 150°C under 600 psi hydrogen for 5 hours. After allowing the mixture to cool to room temperature, the contents of the bomb are dissolved in methanol and filtered through celite. The filtrate is evaporated in vacuo and the residue is taken up in ether and treated with an excess of dry hydrogen chloride gas. The resulant solid is collected by filtration and recrystallized from methanol-acetone to yield the product N-(3-isopropoxypropyl)-N'-(2-octyl)-p-phenylenediamine in dihydrochloride salt form (mp 200°-202°C).

Quelle