Reaktion #426532

Reaktionsgleichung

Potassium hydroxide

ethanol

4-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide

chloroethanol

→

N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide

Ausbeute 39.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated down
2. 2
   workup.DISSOLUTIONdissolved in 5% citric acid
3. 3
   workup.STIRRINGThe mixture was stirred for 1 hour
4. 4
   ExtraktionThe aqueous mixture was extracted three times with ethyl acetate
5. 5
   WaschenThe combined ethyl acetate was washed with water
6. 6
   Trocknendried down over sodium sulfate
7. 7
   EinengenThe organic layer was concentrated down
8. 8
   Sonstigepurified by HPLC

Vorschrift

Potassium hydroxide (4 mmol) was dissolved in ethanol (5 mL) and heated at 80° C. 4-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide (example 58) (1 mmol) was added into the solution followed by chloroethanol (3 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated down and dissolved in 5% citric acid. The mixture was stirred for 1 hour. The aqueous mixture was extracted three times with ethyl acetate. The combined ethyl acetate was washed with water and dried down over sodium sulfate. The organic layer was concentrated down and purified by HPLC to yield 39% of N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide. MS (M+H, 308.25).

Quelle