반응 #64748

반응 방정식

HCl

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

sodium cyanide

ammonium carbonate

ethanol

→

hydantoin

수율 71.0%

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

수율 71.0%

용매

water

반응 조건

후처리

1. 1
   온도The reaction is cooled
2. 2
   추출the product extracted 2×ethyl acetate
3. 3
   세척The collected organics are washed with water, brine
4. 4
   농축concentrated in vacuo
5. 5
   건조The solid isredissolved in ethyl acetate, dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타the resulting crude oil triturated from ether

실험 절차

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.

출처