Reacción #332114

Ecuación de reacción

sulfuric acid

1-(4-hexylphenyl)ethanone

acetic acid

→

desired product

Rendimiento 66.3%

2-(4-hexylphenyl)acetic acid

Rendimiento 66.3%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux
2. 2
   OtroAfter completion of the reaction
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   SecadoThe resulting organic layer was dried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónthe filtrate was concentrated under reduced pressure
7. 7
   OtroThe resulting residue was purified by silica gel column chromatography

Procedimiento

12.0 g (39.3 mmol) of 1-(4-hexylphenyl)ethanone was dissolved in 23.6 g (393 mmol) of glacial acetic acid, mixed with 4.95 g (275 mmol) of water and 5.79 g (58.9 mmol) of sulfuric acid and heated at 150° C. for 6.5 hours under reflux. After completion of the reaction, the reaction solution was diluted with 400 mL of water and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (1:20 to 1:4) as the eluent to give 5.74 g of the desired product as white crystals.

Fuente