Reaction #2045065

Reaction equation

Ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate

THF

→

4-(2,2,3-trimethylcyclopentyl)butanoic acid

Yield 87.6%

Solvents

NaOH

NaOH

Conditions

Workup

1. 1
   OtherUpon completion of the reaction
2. 2
   Washthe aqueous layer washed twice with MTBE (50 ml×2)
3. 3
   workup.ADDITIONThe aqueous layer was treated with aqueous 1.0 N HCl until it
4. 4
   Extractionextracted three times with AcOEt (50 ml×3)
5. 5
   ConcentrationThe combined AcOEt extracts were concentrated in vacuo
6. 6
   Otherpurified via flash column chromatography with (0-40% gradient)

Procedure

Ethyl 4-(2,2,3-trimethylcyclopentyl)butanoate (5 g, 22 mmol) was added to THF (25 ml) into a round bottom flask. Aqueous 1 N NaOH (25 ml) was then added to the flask and the reaction mixture was refluxed at 110° C. for 8 h. Upon completion of the reaction, the reaction mixture was diluted with 1 N NaOH (25 ml) and the aqueous layer washed twice with MTBE (50 ml×2). The aqueous layer was treated with aqueous 1.0 N HCl until it reached a pH of about 3 (for example from 2 to 4), then extracted three times with AcOEt (50 ml×3). The combined AcOEt extracts were concentrated in vacuo and purified via flash column chromatography with (0-40% gradient) to give 4-(2,2,3-trimethylcyclopentyl)butanoic acid as a colorless oil (3.82 g, 87%). The NMR data is indicated below.

Source