Potassium Hydroxide → (6-Chloro-2-ethyl-2-methyl-2,3-dihydro-1H-inden-5-yl)acetic acid

HRID 261542Notes

Reaction equation

HRID 261542 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:20])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[CH2:12][C:11]([CH2:18][CH3:19])([CH3:17])[CH2:10]2>O.CO>[CH2:18]([C:11]1([CH3:17])[CH2:10][C:9]2[C:13](=[CH:14][C:15]([Cl:16])=[C:7]([CH2:6][C:5]([OH:20])=[O:4])[CH:8]=2)[CH2:12]1)[CH3:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53931433HCID 53931433, compound

Product 1

HCID 20394419(6-Chloro-2-ethyl-2-methyl-2,3-dihydro-1H-inden-5-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 20 g of potassium hydroxide in 40 cc of water is added to a solution of 11.5 g of 2-ethyl-6-chloro-2-methyl-5-indanacetic acid methyl ester in 250 cc of methanol, and the solution is boiled at reflux for one hour. The cooled solution is concentrated, diluted with water and the neutral components are extracted with ether. The aqueous phase is acidified with hydrochloric acid, extracted with ether, the ether extract is washed with water, dried over sodium sulphate and concentrated by evaporation. The resulting 2-ethyl-6-chloro-2-methyl-5-indanacetic acid is recrystallized from hexane and has a M.P. of 87°-89°.

Workup

  1. temperatureat reflux for one hour
  2. concentrationThe cooled solution is concentrated
  3. additiondiluted with water
  4. extractionthe neutral components are extracted with ether
  5. extractionextracted with ether
  6. extractionthe ether extract
  7. washis washed with water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated by evaporation
  10. customThe resulting 2-ethyl-6-chloro-2-methyl-5-indanacetic acid is recrystallized from hexane

Sources & evidence

ORD record
ord-12a704a9055f43ae94b8f6baaf13e640
Source dataset
uspto-grants-1979_08
Patent number
US04166131

Reaction notes

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