Reacción #2254193

Ecuación de reacción

dichloromethane

6-propyloxy-1-hexanol

PDC

dichloromethane

sodium acetate

PDC

→

6-propyloxy-1-hexanal

Rendimiento 71.9%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer
2. 2
   workup.STIRRINGstirred overnight
3. 3
   OtroThe progress of reaction
4. 4
   OtroAfter completion of the reaction
5. 5
   Lavadoto elute the product from the column
6. 6
   workup.ADDITIONAll fractions containing the desired pure product
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

a 50-mL, one-necked, round-bottom flask equipped with a magnetic stirrer was charged with 6-propyloxy-1-hexanol (1.0 g), PDC (4.7 g), dichloromethane (10 mL), Celite (1.0 g), and sodium acetate (100 mg). The reaction mixture was stirred at room temperature under nitrogen for 5 minutes. PDC (4.70 g) was added to the reaction mixture, and stirred overnight. The progress of reaction was monitored by TLC (Note 1). After completion of the reaction, the reaction mixture was directly loaded on the column (230-400 mesh silica gel). A solvent gradient of dichloromethane in ethyl acetate (10-20%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure 6-propyloxy-1-hexanal (lot D-1029-050, 710 mg, 71%). Completion of the reaction was monitored by thin layer chromatography (TLC); (eluent: 60% ethyl acetate in hexanes).

Fuente