Reacción #322899

Ecuación de reacción

4-tetradecyl phenol

sodium hydride

dimethylformamide

1,3-dioxolane

→

desired title compound

3-(4-Tetradecylphenoxy)-1,2-propanediol

Disolventes

hexane

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed about 11/2 hours
2. 2
   Temperaturato cool
3. 3
   Lavadowashed with water and brine
4. 4
   Otroevaporated
5. 5
   TemperaturaThe residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour
6. 6
   Temperaturacooled
7. 7
   Otropartially evaporated
8. 8
   Otrothe solid collected
9. 9
   Otrorecrystallized from methanol

Procedimiento

An about 43.5 g portion of 4-tetradecyl phenol was added in portions to a suspension of about 10.8 g of prewashed sodium hydride in dimethylformamide. The mixture was refluxed about 11/2 hours, allowed to cool and about 37.8 g of 2,2-dimethyl-4-[[methylsulfonyl)oxy]methyl]-1,3-dioxolane was added. This mixture was heated to about 80° C. for about 24 hours; diluted with hexane and ether, washed with water and brine and evaporated. The residue was heated on a steam bath with about 500 ml of methanol and about 80 ml of dilute hydrochloric acid for one hour, cooled, partially evaporated, the solid collected and recrystallized from methanol, giving about 38 g of the desired title compound, mp 81.5°-83.5° C.

Fuente