Reacción #334745

Ecuación de reacción

hexamethylene tetramine

sodium iodide

4-chloromethylbenzocyclobutene

ethanol

→

4-formylbenzocyclobutene

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux for 2 h
3. 3
   workup.DISTILLATIONdistilled
4. 4
   Extracciónthe distillate was extracted three times with ether
5. 5
   ExtracciónThe combined ether extract
6. 6
   Lavadowas washed with water
7. 7
   Secadodried over magnesium sulfate
8. 8
   workup.DISTILLATIONfractionally distilled

Procedimiento

To a hot solution of hexamethylene tetramine (14 g) and sodium iodide (16 g) in 140 g of ethanol was added 4-chloromethylbenzocyclobutene (15.2 g) with stirring. After standing at ambient temperature for 2-3 h, the mixture was diluted with 150 ml of water and then heated at reflux for 2 h. The resulting mixture was steam distilled and the distillate was extracted three times with ether. The combined ether extract was washed with water, dried over magnesium sulfate, and fractionally distilled to give 4-formylbenzocyclobutene: 1H NMR (CDCl3) δ 3.17 (s, 4), 7.15 (d, 1), 7.51 (s, 1), 7.67 (d, 1) and 9.86 ppm (s, 1).

Fuente