Reaction #50784

Reaction equation

2-(carboethoxy)indan

potassium hydroxide

→

2-indancarboxylic acid

Yield 69.1%

Solvents

ethanol

water

Conditions

Workup

1. 1
   OtherPartition between water (150 mL) and ethyl ether (2×150 mL)
2. 2
   ExtractionExtract with methylene chloride (2×150 mL)
3. 3
   Dryingdry (Na2SO4)
4. 4
   Otherevaporate the solvent in vacuo

Procedure

Dissolve 2-(carboethoxy)indan (6.49 g, 34.1mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17 mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 2-indancarboxylic acid as a tan solid (3.82 g, 69%).

Source