Reacción #2775

Ecuación de reacción

hydroquinone

methacryloyl chloride

→

hydroquinone monomethacrylate

Disolventes

pyridine

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintained at 0° to 5° C
2. 2
   workup.STIRRINGAfter stirring for one more hour at room temperature
3. 3
   Otrothe acetone was evaporated
4. 4
   workup.ADDITIONWater was then added
5. 5
   Extracciónwith ether extraction
6. 6
   LavadoAfter washing this ether layer with a 5% aqueous solution of sodium hydrogencarbonate
7. 7
   Lavadothe solution was then washed with water
8. 8
   Secadodried (anhydrous sodium carbonate)
9. 9
   OtroThe ether was then evaporated out, with a white solid being
10. 10
    Otroobtained
11. 11
    OtroThis was recrystallized from water

Procedimiento

350 g of hydroquinone was dissolved in 2.5 kg of acetone and 500 ml of pyridine. After cooling to 0° C., 313.5 g of methacryloyl chloride was added dropwise, with the reaction temperature maintained at 0° to 5° C. Stirring was then carried out for 3 hours at the same temperature. After stirring for one more hour at room temperature, the acetone was evaporated. Water was then added, and hydrochloric acid was used to adjust the solution to an acidic pH (pH 4), with ether extraction then performed. After washing this ether layer with a 5% aqueous solution of sodium hydrogencarbonate, the solution was then washed with water and dried (anhydrous sodium carbonate). The ether was then evaporated out, with a white solid being obtained. This was recrystallized from water, to obtain 420 g of colorless, needle crystals of hydroquinone monomethacrylate having a melting point of 120.5° to 121.5° C.

Fuente