Reacción #54665

Ecuación de reacción

p-menth-3-oyl chloride

diethanolamine

→

N,N-Bis(2-hydroxyethyl)-p-menthane-3-carboxamide

Disolventes

chloroform

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe yellow oil (upper layer) was separated
2. 2
   OtroRemoval of the chloroform
3. 3
   workup.WAITleft a viscous oil (6 g.)
4. 4
   OtroThis was separated by column chromatography on neutral alumina (activity 1)
5. 5
   LavadoEluting with chloroform (200 ml.)
6. 6
   Otroremoved the minor component
7. 7
   Lavadothe major product was eluted from the column with chloroform+5% methanol

Procedimiento

A solution of p-menth-3-oyl chloride (4.0 g., 0.020 moles) in chloroform (30 ml.) was added dropwise to a stirred solution of diethanolamine (4.2 g., 0.044 moles) in chloroform (50 ml.). The reaction mixture goes cloudy and a yellow oil separates out. After 2 hours at room temperature, the yellow oil (upper layer) was separated. Infra red spectographic analysis indicated this to be (HOCH2CH2)2NH2+Cl-. Removal of the chloroform left a viscous oil (6 g.). Thin layer chromatography (CHCl3 and CHCl3 +10% CH3OH) indicated it to consist of one major component and a minor component of larger Rf value. This was separated by column chromatography on neutral alumina (activity 1). Eluting with chloroform (200 ml.) removed the minor component and the major product was eluted from the column with chloroform+5% methanol. The major component was shown to be N,N-bis(2-hydroxyethyl)-p-menthane-3-carboxamide.

Fuente