반응 #361684

반응 방정식

sodium nitrite

5'-amino-3',4'-dimethoxyacetophenone

copper(I) cyanide

potassium cyanide

→

5'-cyano-3',4'-dimethoxyacetophenone

용매

water

water

methylene chloride

hydrochloric acid

반응 조건

후처리

1. 1
   workup.ADDITIONare added
2. 2
   여과filtered
3. 3
   기타The organic phase is separated
4. 4
   세척washed with water
5. 5
   건조dried over sodium sulfate
6. 6
   기타evaporated
7. 7
   기타The residue is recrystallized from methylene chloride/petroleum ether

실험 절차

A solution of 5.2 g of sodium nitrite in 20 ml of water is added dropwise at 0° within 20 minutes to 14.0 g of 5'-amino-3',4'-dimethoxyacetophenone dissolved in 155 ml of 1N hydrochloric acid. After stirring at -2° for 30 minutes the cold diazonium salt solution is added dropwise within 30 minutes at 5°-10° to a solution of 8.7 g of copper(I) cyanide and 5.45 g of potassium cyanide in 60 ml of water. After completion of the addition 200 ml of methylene chloride are added, and the reaction mixture is stirred at 23° for 3 hours and then filtered. The organic phase is separated, washed with water, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 5'-cyano-3',4'-dimethoxyacetophenone of m.p. 125°-126°.

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