Reaktion #81713

Reaktionsgleichung

ammonium chloride

sodium hydride

methyl 2-(4'-hydroxymethylphenyl)benzoate

p-toluenesulfonyl chloride

→

title compound

Ausbeute 82.4%

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

Ausbeute 82.4%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   workup.WAITThen, the reaction was effected at room temperature for 2 hours
3. 3
   Temperaturfurther reflux
4. 4
   Temperaturby heating
5. 5
   workup.WAITwas effected for 4 hours
6. 6
   SonstigeThe reaction liquid
7. 7
   Temperaturwas cooled
8. 8
   ExtraktionThe resulting mixture was extracted with chloroform (200 ml)
9. 9
   WaschenAfter the organic phase was washed with water
10. 10
    Sonstigedried
11. 11
    Einengenit was subjected to vacuum concentration
12. 12
    SonstigeThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Vorschrift

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%).

Quelle