Sodium Hydroxide → 5,6-dimethoxy-1H-indene-2-carboxylic Acid

HRID 2175694Notes

Reaction equation

HRID 2175694 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][C:7]([C:14]([O:16]C)=[O:15])=[CH:6]2.[OH-].[Na+]>C1COCC1.CO>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][C:7]([C:14]([OH:16])=[O:15])=[CH:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12423472methyl 5,6-dimethoxy-1H-indene-2-carboxylate

Product 1

HCID 103761625,6-dimethoxy-1H-indene-2-carboxylic AcidYield 48.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5,6-dimethoxy-1H-indene-2-carboxylate (330 mg, 1.41 mmol) in THF (8 mL) and MeOH (4 mL) was added 2 N NaOH solution (3.5 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature for 2 hours and the reaction was quenched with 1N HCl solution. Then mixture was diluted with water and the resulting suspension was filtered and the solid was dried under vacuum to give 5,6-dimethoxy-1H-indene-2-carboxylic acid (150 mg, 48%). LC-MS (ES-API); rt 8.44 min; m/z calculated for C12H12O4 [M−H]− 219.1, found 219.1.

Workup

  1. customthe reaction was quenched with 1N HCl solution
  2. additionThen mixture was diluted with water
  3. filtrationthe resulting suspension was filtered
  4. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-b0ad512fc3d644aa91851d20b059e618
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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