تفاعل #463226

معادلة التفاعل

Dimethyl sulfate

2-phenoxybenzaldoxime

chlorine

potassium carbonate

dimethylformamide

→

α-methoxyimino-2-phenoxyphenylacetonitrile

المردود 16.6%

المذيبات

ether

ether

water

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas introduced into the mixture below -10° C.
2. 2
   أخرىAfter the completion of the reaction
3. 3
   تركيزthe reaction mixture was concentrated under reduced pressure
4. 4
   workup.STIRRINGthe mixture was stirred overnight
5. 5
   workup.ADDITIONwas added to the reaction mixture, which
6. 6
   استخلاصwas extracted with methylene chloride
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   أخرىpurified by silica gel chromatography (ethyl acetate/n-hexane)
9. 9
   أخرىto obtain crude α-hydroxyimino-2-phenoxyphenylacetonitrile (0.51 g)
10. 10
    workup.STIRRINGwas stirred at room temperature for 2 hours
11. 11
    workup.ADDITIONwas added to the reaction mixture, which
12. 12
    غسيلwas washed twice with water
13. 13
    تجفيفdried over anhydrous magnesium sulfate
14. 14
    تركيزconcentrated under reduced pressure
15. 15
    أخرىThe crude product thus obtained
16. 16
    أخرىwas purified by silica gel chromatography (ethyl acetate/n-hexane)

الإجراء التجريبي

To 2-phenoxybenzaldoxime (1.07 g, 0.005 mole) was added dried ether (10 ml), and chlorine (0.46 g, 0.0065 mole) was introduced into the mixture below -10° C. followed by stirring at 0° C. for 5 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then, dried methylene chloride (10 ml) and tetraethylammonium cyanide (0.86 g, 0.0055 mole) were added to the resulting residue and the mixture was stirred overnight. After completion of the reaction, water (150 ml) was added to the reaction mixture, which was extracted with methylene chloride, dried over anhydrous magnesium sulfate and purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain crude α-hydroxyimino-2-phenoxyphenylacetonitrile (0.51 g), to which were added dried dimethylformamide (4 ml) and potassium carbonate (0.36 g, 0.0026 mole). Dimethyl sulfate (0.30 g, 0.0024 mole) was further added to the mixture, which was stirred at room temperature for 2 hours. After completion of the reaction, ether (100 ml) was added to the reaction mixture, which was washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product thus obtained was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain α-methoxyimino-2-phenoxyphenylacetonitrile (0.21 g, yield: 16.6%) as a colorless oil.

المصدر