Reacción #67610

Ecuación de reacción

potassium carbonate

3,4-dihydroxy benzaldehyde

cyclopentyl bromide

potassium carbonate

→

4-cyclopentyloxy-3-hydroxy benzaldehyde

Disolventes

toluene

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to ambient temperature
2. 2
   Filtraciónfiltered
3. 3
   Otroto remove inorganic materials
4. 4
   OtroThe residue obtained after concentration of the filtrate
5. 5
   Extracciónextracted with 5-10% aqueous sodium hydroxide solution (6×50 mL)
6. 6
   OtroThe solid which separated
7. 7
   Filtraciónwas filtered
8. 8
   Lavadowashed with water
9. 9
   Otrodried

Procedimiento

A suspension of 3,4-dihydroxy benzaldehyde (50.0 g, 0.3623 mol), cyclopentyl bromide (135 g, 0.9058 mol) and potassium carbonate (50.0 g, 0.3623 mol) in N,N-dimethylformamide (500 mL) was stirred at about 75-80° C. for about 1.0 hr. 4×12.5 g potassium carbonate was then added after every 1.0 hr. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic materials. The residue obtained after concentration of the filtrate was diluted with toluene (250 mL), and extracted with 5-10% aqueous sodium hydroxide solution (6×50 mL). The combined aqueous layer was acidified to pH about 3 to 5 by 5N aqueous hydrochloric acid solution. The solid which separated was filtered, washed with water and dried to give 4-cyclopentyloxy-3-hydroxy benzaldehyde.

Fuente