Reacción #63968

Ecuación de reacción

nitric acid

2,3-dihydro-2,2-dimethylbenzofuran

→

2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran

Disolventes

sulfuric acid

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter complete addition the mixture
2. 2
   Extracciónthe total extracted with diethyl ether
3. 3
   SecadoThe extract was dried over anhydrous magnesium chloride
4. 4
   Filtraciónfiltered
5. 5
   OtroEvaporation of the filtrate under reduced pressure
6. 6
   Otroproduced a black oil
7. 7
   OtroPurification of this oil by column chromatography on silica gel eluting with toluenen-hexane (9:1)

Procedimiento

During a one hour period an ice cold mixture of 43 mL concentrated nitric acid and 50 mL of concentrated sulfuric acid was added dropwise to 100.0 g (0.67 mole) 2,3-dihydro-2,2-dimethylbenzofuran while maintaining the temperature of 5° C. After complete addition the mixture was stirred at 0° C. for 2.5 hours. The reaction mixture was poured into ice water and the total extracted with diethyl ether. The extract was dried over anhydrous magnesium chloride and filtered. Evaporation of the filtrate under reduced pressure produced a black oil. Purification of this oil by column chromatography on silica gel eluting with toluenen-hexane (9:1), yielded 50.0 g of 2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran as a solid.

Fuente