HCID 53711725, compound → HCID 54196325, compound

HRID 275726Notes

Reaction equation

HRID 275726 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][C:8]([C:19]([O:21]CC)=[O:20])([C:14]([O:16]CC)=[O:15])[CH2:9]2)[CH3:3]>[OH-].[K+]>[CH3:3][CH:2]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][C:8]([C:19]([OH:21])=[O:20])([C:14]([OH:16])=[O:15])[CH2:9]2)[CH3:1]

Participants

3

Reactant 1

HCID 53711725HCID 53711725, compound

Product 1

HCID 54196325HCID 54196325, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution/suspension of diethyl 4-(2-propyl)oxyindan-2,2-dicarboxylate (11.5 g) in potassium hydroxide solution (50 ml, 3 M) was heated at reflux for 18 hours. The solution was cooled to room temperature and was extracted with ether. The aqueous was acidified to pH<1 with aqueous hydrochloric acid (3 M) and was extracted with ethyl acetate. The standard workup afforded 4-(2-propyl)oxyindan-2,2-dicarboxylic acid (8.5 g) as a brown solid, which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. extractionwas extracted with ether
  4. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-be47e1e408344b4cbcb8004bbc533253
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

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