Reaction #54873

Reaction equation

ethyl 4-(4-acetyl-4-ethoxycarbonyl-8-acetoxytridec-6-en-1-yl)benzoate

sodium hydroxide

→

4-(4-Acetyl-8-hydroxytridec-6-en-1-yl)benzoic acid

Solvents

ethanol

water

Conditions

Workup

1. 1
   Temperatureunder reflux for 3 hours
2. 2
   OtherSolvents are removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue is dissolved in water
4. 4
   Extractionthe solution extracted with ether
5. 5
   OtherIt is isolated in pure condition by column chromatography on silica gel with 4% methanol in chloroform as the eluant

Procedure

A solution of ethyl 4-(4-acetyl-4-ethoxycarbonyl-8-acetoxytridec-6-en-1-yl)benzoate (50.2 g., 0.1 mole) and sodium hydroxide (28.0 g., 0.7 mole) in water (300 ml.) and ethanol (350 ml.) is boiled under reflux for 3 hours. Solvents are removed under reduced pressure, the residue is dissolved in water, and the solution extracted with ether. The aqueous layer is acidified with concentrated hydrochloric acid to the Congo Red endpoint. The crude product separates as an oil. It is isolated in pure condition by column chromatography on silica gel with 4% methanol in chloroform as the eluant. 4-(4-Acetyl-8-hydroxytridec-6-en-1-yl)benzoic acid is obtained as a yellow, very viscous oil.

Source