Reaction #217158

Reaction equation

ethyl-6-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethynyl]2-naphthoate

Compound 2

ethyl-6-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethynyl]2-naphthoate

KOH

→

title product

6-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethynyl]-2-naphthoic acid

Solvents

ethanol

ethanol

water

Conditions

Workup

1. 1
   Othersolvent was removed in-vacuo
2. 2
   workup.ADDITIONthe residue treated with 1 ml of water
3. 3
   Extractionextracted with 1×3 ml portions of ether
4. 4
   Extractionextracted with 3×3 ml portions of ether
5. 5
   DryingCombined ether extracts were dried (MgSO4)
6. 6
   Concentrationconcentrated in-vacuo

Procedure

To a stirred solution of 0.130 g (0.38 mmol) of ethyl-6-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethynyl]2-naphthoate (Compound 2) in 0.7 ml of ethanol was added dropwise under nitrogen 0.9 ml of a 1.86M solution of KOH in ethanol and water. After being stirred at 50 degrees C. for 18 hours, solvent was removed in-vacuo and the residue treated with 1 ml of water and extracted with 1×3 ml portions of ether. The aqueous layer was then acidified with dilute HCl and extracted with 3×3 ml portions of ether. Combined ether extracts were dried (MgSO4) and concentrated in-vacuo to give the title product.

Source