Reacción #55561

Ecuación de reacción

2-(6-carboxyhexyl)-3-nitromethyl-cyclopentan-1-one

p-toluenesulphonic acid

water

→

1-ethylenedioxy-2-(6-carboxyhexyl)-3-nitromethyl-cyclopentane

Disolventes

benzene

ethylene glycol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrois separated in a Marcusson apparatus
2. 2
   LavadoThe mixture is washed with an aqueous saturated NaHCO3 -solution (50 ml.)
3. 3
   Secadowith water to neutrality, dried over sodium sulphate
4. 4
   Otrothe solvent is evaporated in vacuo
5. 5
   LavadoFrom the oily residue, by chromatography on silica (300 g.) and elution with benzene/ethyl acetate (6:1), 13 g

Procedimiento

The solution of 2-(6-carboxyhexyl)-3-nitromethyl-cyclopentan-1-one, methyl ester (14 g.) in benzene (200 ml.), ethylene glycol (16.1 ml.), p-toluenesulphonic acid (0.315 g.), is heated to boiling for 16 hours. The reaction water is separated in a Marcusson apparatus. The mixture is washed with an aqueous saturated NaHCO3 -solution (50 ml.), then with water to neutrality, dried over sodium sulphate and the solvent is evaporated in vacuo. From the oily residue, by chromatography on silica (300 g.) and elution with benzene/ethyl acetate (6:1), 13 g. of 1-ethylenedioxy-2-(6-carboxyhexyl)-3-nitromethyl-cyclopentane, methyl ester, are obtained.

Fuente