Reaction #2314281

Reaction equation

hydrochloric acid

sodium hydroxide

nitrile

(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetonitrile

water

→

(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetic acid

Solvents

hydrogen peroxide

Conditions

Workup

1. 1
   Temperatureat reflux overnight
2. 2
   ExtractionThe acid product is extracted with ethyl acetate
3. 3
   Washthe combined organic layers are washed with brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   ConcentrationThe solution is concentrated in vacuo

Procedure

To a solution of sodium hydroxide (10.5 g) in water (150 mL) and 30% hydrogen peroxide (50 mL) is added the nitrile 2A (R=4-Methyl-3-pentenyl) (10 g). The reaction mixture is stirred at reflux overnight. The reaction is then cooled to room temperature, and poured into a mixture of ice (30 g) and hydrochloric acid (22 mL). The acid product is extracted with ethyl acetate, and the combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo.

Source