Reaktion #64748

Reaktionsgleichung

HCl

3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxybenzaldehyde

sodium cyanide

ammonium carbonate

ethanol

→

hydantoin

Ausbeute 71.0%

5-[3-(Bicyclo[2.2.1]hept-2-yloxy]-4-Methoxyphenyl]2,4-Imidazolidinedione

Ausbeute 71.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled
2. 2
   Extraktionthe product extracted 2×ethyl acetate
3. 3
   WaschenThe collected organics are washed with water, brine
4. 4
   Einengenconcentrated in vacuo
5. 5
   TrocknenThe solid isredissolved in ethyl acetate, dried over Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigethe resulting crude oil triturated from ether

Vorschrift

3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxybenzaldehyde (20.0 g, 81.3 mmol), sodium cyanide (8.0 g, 162.6 mmol) and ammonium carbonate (32.0 g, 333.3 mmol) are dissolved in 100 ml ethanol and 100 ml water and refluxed for 4 hours. The reaction is cooled, neutralized with 1N HCl solution and the product extracted 2×ethyl acetate. The collected organics are washed with water, brine and concentrated in vacuo. The solid isredissolved in ethyl acetate, dried over Na2SO4, concentrated in vacuo and the resulting crude oil triturated from ether to produce 18.3 g (71%) of the hydantoin as a crystalline material. This material is a 7:3 endo/exo mixture of bicycloalkyl isomers.

Quelle