Reacción #1880958

Ecuación de reacción

veratrol

vinylacetic acid

→

5,6-dimethoxy-3-methylindan-1-one

Rendimiento 74.0%

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter 30 minutes (min) of stirring
2. 2
   Extracciónthe product was extracted three times
3. 3
   LavadoThe combined organic phases were washed twice
4. 4
   Secadoeach time with 100 ml of 2N NaOH, once with 100 ml of water and once with 50 ml of saturated sodium chloride solution, dried over sodium sulfate
5. 5
   Otrofreed from solvent on a rotary evaporator
6. 6
   OtroAfter recrystallizing the residue (in AcOEt/pentane)

Procedimiento

A mixture of 19.1 ml (150 mmol) of veratrol and 19.2 ml (225 mmol) of vinylacetic acid in 230 g of 83% polyphosphoric acid was stirred for 15 h at 60° C. and then poured into 500 ml of ice water. After 30 minutes (min) of stirring, the product was extracted three times, each time with 200 ml of ether. The combined organic phases were washed twice, each time with 100 ml of 2N NaOH, once with 100 ml of water and once with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and freed from solvent on a rotary evaporator. After recrystallizing the residue (in AcOEt/pentane), 22.8 g (74%) of 5,6-dimethoxy-3-methylindan-1-one were obtained.

Fuente