Reacción #1253190

Ecuación de reacción

potassium carbonate

potassium iodide

vanillin

6-chlorohexanol

→

4-(6-hexyloxy)-3-methoxybenzaldehyde

Rendimiento 84.5%

Disolventes

water

dimethyl sulphoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is then cooled to room temperature
2. 2
   Extracciónextracted three times with 150 ml of ethyl acetate each time
3. 3
   LavadoThe combined organic phases are washed twice with 200 ml of water each time
4. 4
   Secadodried over magnesium sulphate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroPurification of the residue by chromatography on 400 g of silica gel

Procedimiento

41.45 g (300 mmol) of potassium carbonate and 27.4 g (165 mmol) of potassium iodide are added to a solution of 22.8 g (150 mmol) of vanillin and 30.7 g (225 mmol) of 6-chlorohexanol in 500 ml of dimethyl sulphoxide (DMSO) and the mixture is stirred overnight at 60° C. under nitiogen. The mixture is then cooled to room temperature, poured into 600 ml of water and extracted three times with 150 ml of ethyl acetate each time. The combined organic phases are washed twice with 200 ml of water each time, dried over magnesium sulphate, filtered and concentrated. Purification of the residue by chromatography on 400 g of silica gel using cyclohexane/ethyl acetate 1:1 yields 29.95 g of 4-(6-hexyloxy)-3-methoxybenzaldehyde.

Fuente