Potassium Hydroxide → 2-Indancarboxylic Acid

HRID 260681

Reaction equation

HRID 260681 reaction equation
[C:1]([CH:6]1[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-].[K+]>C(O)C.O>[CH2:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[C:1]([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15280733ethyl 2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 5757772-Indancarboxylic AcidYield 69.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dissolve 2-(carboethoxy)indan (6.49 g, 34.1 mmol) in ethanol (95%, 150 mL) and water (75 mL). Add potassium hydroxide (9.5 g, 0.17mol) and stir at room temperature for 1 hour. Partition between water (150 mL) and ethyl ether (2×150 mL). Acidify the aqueous phase with hydrochloric acid to pH 1. Extract with methylene chloride (2×150 mL), dry (Na2SO4) and evaporate the solvent in vacuo to give 2-indancarboxylic acid as a tan solid (3.82 g, 69%).

Workup

  1. customPartition between water (150 mL) and ethyl ether (2×150 mL)
  2. extractionExtract with methylene chloride (2×150 mL)
  3. dry with materialdry (Na2SO4)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-fe2f626c6e61460481edd264f8a074f4
Source dataset
uspto-grants-1996_06
Patent number
US05529996

Linked notes

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