Reacción #651852

Ecuación de reacción

2-fluoro-4-(3-methyl-3-hydroxy-1-butynyl)toluene

sodium hydroxide

benzene

→

2-fluoro-4-ethynyltoluene

Rendimiento 40.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 3 hours
2. 2
   TemperaturaAfter cooling
3. 3
   FiltraciónInsoluble materials were filtered away with Celite (trade name of Johns-Manville Company)
4. 4
   Secadothe residue was dried over anhydrous magnesium sulfate
5. 5
   OtroThe drying agent was separated away
6. 6
   workup.DISTILLATIONthe solvent was carefully distilled away from the solution under reduced pressure
7. 7
   Otrothe residue was purified by silica gel chromatography (elution liquid: hexane)
8. 8
   workup.DISTILLATIONdistilled away the solvent under reduced pressure (boiling point: 100° C., 20 mmHg)

Procedimiento

The mixture of 2-fluoro-4-(3-methyl-3-hydroxy-1-butynyl)toluene (0.035 mol), sodium hydroxide (0.07 mol), and benzene 40 ml was refluxed for 3 hours. After cooling, water 40 ml was added and the mixture was thoroughly stirred. Insoluble materials were filtered away with Celite (trade name of Johns-Manville Company), and the residue was dried over anhydrous magnesium sulfate. The drying agent was separated away, the solvent was carefully distilled away from the solution under reduced pressure, the residue was purified by silica gel chromatography (elution liquid: hexane) and then distilled away the solvent under reduced pressure (boiling point: 100° C., 20 mmHg) to obtain cororless oily 2-fluoro-4-ethynyltoluene (0.014 mol).

Fuente