Reaction #4072

Reaction equation

(S)-2-(5-chloro-6-methoxy-2-naphthyl)-propionic acid

→

(S)-2-(6-methoxy-2-naphthyl)propionic acid

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   Filtrationit is filtered
2. 2
   workup.ADDITIONdiluted with excess dilute hydrochloric acid
3. 3
   Extractionextracted with methylene chloride
4. 4
   OtherThe organic phase is evaporated to dryness
5. 5
   Otherthe residue recrystallized from methylene chloride/hexane

Procedure

A solution of 1 g of (S)-2-(5-chloro-6-methoxy-2-naphthyl)-propionic acid in 20 ml of 10% aqueous sodium hydroxide solution at 90° C. is treated with 3 g of a nickel-aluminum alloy in small portions. After stirring the mixture for two hours, it is filtered, diluted with excess dilute hydrochloric acid and extracted with methylene chloride. The organic phase is evaporated to dryness and the residue recrystallized from methylene chloride/hexane to yield (S)-2-(6-methoxy-2-naphthyl)propionic acid after recrystallization.

Source