Ethanol → (2-Ethyl-2,3-dihydro-1H-inden-5-yl)acetic acid

HRID 261541Notes

Reaction equation

HRID 261541 reaction equation
[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](CC#N)[CH:9]=2)[CH2:4]1)[CH3:2].[OH-:15].[K+].[CH2:17]([OH:19])[CH3:18]>O>[CH2:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:18][C:17]([OH:15])=[O:19])[CH:9]=2)[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12627904(2-Ethyl-2,3-dihydro-1H-inden-5-yl)acetonitrile

Product 1

HCID 12627894(2-Ethyl-2,3-dihydro-1H-inden-5-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.8 g of 2-ethyl-5-indan-acetonitrile are dissolved in 350 cc of ethanol, a solution of 26.7 g of potassium hydroxide in 45 cc of water is added, and the mixture is boiled at reflux for 20 hours. The solution is concentrated to 50 cc, diluted with water and extracted with ether, and the ether phase is discarded. The aqueous phase is then acidified with 2 N hydrochloric acid and extracted with ether. The crude 2-ethyl-5-indanacetic acid, obtained after concentrating the ether extract, is purified by chromatography on a 50-fold quantity of silica gel using chloroform containing 1.5% of methanol as eluant. After recrystallization from hexane the title compound has a M.P. of 44°-46°.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe solution is concentrated to 50 cc
  3. additiondiluted with water
  4. extractionextracted with ether
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-3282f30a06dd4dd0b61c7f476d4799ca
Source dataset
uspto-grants-1979_08
Patent number
US04166131

Reaction notes

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