Lithium Hydroxide → 2-Indancarboxylic Acid

HRID 37377

Reaction equation

HRID 37377 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 between ethyl acetate and 6N hydrochloric acid. Separate the organic phase and wash with brine. Dry (MgSO4) and evaporate the solvent i n 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 i n vacuo
  8. customto give an off-white solid
  9. distillationDistill (120°-160° C. @0 .2-0.5 mmHg)

Sources & evidence

ORD record
ord-925e6b2b9f4843428e1f54535f85a285
Source dataset
uspto-grants-1995_05
Patent number
US05420271

Linked notes

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