Reacción #81713

Ecuación de reacción

ammonium chloride

sodium hydride

methyl 2-(4'-hydroxymethylphenyl)benzoate

p-toluenesulfonyl chloride

→

title compound

Rendimiento 82.4%

methyl 2-(4'-p-toluenesulfonyloxymethylphenyl)benzoate

Rendimiento 82.4%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder cooling with ice
2. 2
   workup.WAITThen, the reaction was effected at room temperature for 2 hours
3. 3
   Temperaturafurther reflux
4. 4
   Temperaturaby heating
5. 5
   workup.WAITwas effected for 4 hours
6. 6
   OtroThe reaction liquid
7. 7
   Temperaturawas cooled
8. 8
   ExtracciónThe resulting mixture was extracted with chloroform (200 ml)
9. 9
   LavadoAfter the organic phase was washed with water
10. 10
    Otrodried
11. 11
    Concentraciónit was subjected to vacuum concentration
12. 12
    OtroThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Procedimiento

10.0 g (41 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in tetrahydrofuran (200 ml). 2.0 g (50 mmol) of a 60% sodium hydride was added thereto under cooling with ice, followed by stirring for one hour. A solution of 8.65 g (45.4 mmol) of p-toluenesulfonyl chloride in tetrahydrofuran (50 ml) was dropwise added thereto. Then, the reaction was effected at room temperature for 2 hours and further reflux by heating was effected for 4 hours. The reaction liquid was cooled and added to a saturated aqueous solution of ammonium chloride. The resulting mixture was extracted with chloroform (200 ml). After the organic phase was washed with water and dried, it was subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 13.4 g of the title compound as a wax (yield 82%).

Fuente