Lithium Hydroxide → 2-Indancarboxylic Acid

HRID 1451239Notes

Reaction equation

HRID 1451239 reaction equation
[C:1]([C:6]1(C(OCC)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([O:3]CC)=[O:2].[OH-].[Li+]>C(O)C>[C:1]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 110107772,2-Dicarboethoxy-indane

Product 1

HCID 5757772-Indancarboxylic AcidYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2,2-dicarboethoxy-indane (5.67 g, 21.7 mmol) in ethanol (150 mL). Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature. Reflux for 1 hour and concentrate the solution in vacuo. Partition between ethyl acetate and 6N hydrochloric acid. Separate the organic phase and wash with brine. Dry (MgSO4) and evaporate the solvent in vacuo to give an off-white solid. Distill (120°-160° C. @0.2-0.5 mmHg) to give 2-carboxy-indan (2.5 g, 71%).

Workup

  1. temperatureReflux for 1 hour
  2. concentrationconcentrate the solution in vacuo
  3. customPartition between ethyl acetate and 6N hydrochloric acid
  4. customSeparate the organic phase
  5. washwash with brine
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. customto give an off-white solid
  9. distillationDistill (120°-160° C. @0.2-0.5 mmHg)

Sources & evidence

ORD record
ord-068059b48bbc4e4690757566ba7f5ec1
Source dataset
uspto-grants-1997_02
Patent number
US05604221

Reaction notes

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