反应详情

Vanillin (10 g., 66 mmol) in acetonitrile (100 ml) was treated with finely-powdered, anhydrous potassium carbonate (12 g., 87 mmol) with vigorous stirring to yield a mobile suspension. Diethyl sulfate (11 ml, 84 mmol) was added at room temperature. The suspension was brought to reflux, becoming quite thick after 10 minutes, but thinning again after 20 minutes. Refluxing was continued for 48 hours, at which point water (5 ml) was added. After an additional 2 hours of reflux, the mixture was cooled and treated with 500 ml ice water. Stirring at 0° for several hours produced a granular precipitate which was filtered off and washed with water. Air drying afforded 11.5 g. of the product (97%) as an off-white solid melting at 61°-62.5° C. NMR and IR data are listed in Tables 3 and 7. ##STR25##

1. customto yield a mobile suspension
2. temperatureto reflux
3. waitthinning again after 20 minutes
4. temperatureRefluxing
5. additionwas added
6. temperatureAfter an additional 2 hours of reflux
7. temperaturethe mixture was cooled
8. stirringStirring at 0° for several hours
9. customproduced a granular precipitate which
10. filtrationwas filtered off
11. washwashed with water
12. customAir drying
13. customafforded 11.5 g