Reaction #54665

Reaction equation

p-menth-3-oyl chloride

diethanolamine

→

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

Solvents

chloroform

chloroform

Conditions

Workup

1. 1
   Otherthe yellow oil (upper layer) was separated
2. 2
   OtherRemoval of the chloroform
3. 3
   workup.WAITleft a viscous oil (6 g.)
4. 4
   OtherThis was separated by column chromatography on neutral alumina (activity 1)
5. 5
   WashEluting with chloroform (200 ml.)
6. 6
   Otherremoved the minor component
7. 7
   Washthe major product was eluted from the column with chloroform+5% methanol

Procedure

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.

Source