Lithium Hydroxide → 2-Indancarboxylic Acid

HRID 2395973Notes

Reaction equation

HRID 2395973 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-indan (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 betweenethyl acetate and 6N hydrochloric acid. Separate the organic phase and washwith 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 betweenethyl acetate and 6N hydrochloric acid
  4. customSeparate the organic phase
  5. dry with materialDry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customto give an off-white solid
  8. distillationDistill (120°-160° C. @0.2-0.5 mmHg)

Sources & evidence

ORD record
ord-38962027947f4a4281b72db6231a2a57
Source dataset
uspto-grants-1996_02
Patent number
US05491142

Reaction notes

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