反应详情

To 600 mL of toluene in a Morton reaction flask was added 100 g (0.598 mol) of 2-methyl-3-nitrophenylmethanol with stirring. The solution was heated to reflux, and 100 mL of toluene was removed by distillation into a Dean Stark trap. The solution was cooled, and 48.3 mL of pyridine was added. After further cooling with an ice-water bath, 51.6 g (0.658 mol) of acetyl chloride was added dropwise. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature, and was stirred for 16 hours. The reaction mixture was heated under reflux for 3.5 hours, cooled to ambient temperature, then poured over 1 L of ice. When the ice had melted, the organic layer was separated, and the aqueous layer washed with three portions of 300 mL each of toluene. The toluene wash was combined with the organic layer, and the whole was washed with two portions of 250 mL each of aqueous 2 N hydrochloric acid, 250 mL of saturated aqueous solution of sodium chloride, two portions of 250 mL each of an aqueous 2 N solution of sodium hydroxide, and finally, 250 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation using a Kugelrohr distilling system to give 107.3 g of 2-methyl-3-nitrophenylmethyl acetate, b.p. 120° C./0.25 mm.

1. temperatureThe solution was heated
2. temperatureto reflux
3. custom100 mL of toluene was removed by distillation into a Dean Stark trap
4. temperatureThe solution was cooled
5. addition48.3 mL of pyridine was added
6. temperatureAfter further cooling with an ice-water bath
7. additionUpon complete addition
8. stirringwas stirred for 16 hours
9. temperatureThe reaction mixture was heated
10. temperatureunder reflux for 3.5 hours
11. temperaturecooled to ambient temperature
12. customthe organic layer was separated
13. washthe aqueous layer washed with three portions of 300 mL each of toluene
14. washThe toluene wash
15. washthe whole was washed with two portions of 250 mL each of aqueous 2 N hydrochloric acid, 250 mL of saturated aqueous solution of sodium chloride, two portions of 250 mL each of an aqueous 2 N solution of sodium hydroxide
16. dry with materialThe organic layer was dried with magnesium sulfate
17. filtrationfiltered
18. concentrationthe filtrate concentrated under reduced pressure
19. customto give a residual oil
20. distillationThe oil was subjected to distillation
21. distillationdistilling system