Methyl 4-phenyl-2-indancarboxylate → 4-Phenyl-2-indancarboxylic acid

HRID 1106625Notes

Reaction equation

HRID 1106625 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]([C:16]([O:18]C)=[O:17])[CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[OH-].[Na+]>[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]([C:16]([OH:18])=[O:17])[CH2:11]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 18789315Methyl 4-phenyl-2-indancarboxylate

Product 1

HCID 187893104-Phenyl-2-indancarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-bromo-2-indancarboxylate (510 mg), tributylphenyltin (881 mg), a tris(dibenzylideneacetone)dipalladium chloroform complex (41 mg) and tri-2-furylphosphine (19 mg) were dissolved in N-methylpyrrolidone (10 ml), and the mixture was stirred at 70° C. for 3 hours and allowed to cool. To the reaction solution was added a saturated potassium fluoride solution and the solution was stirred at room temperature for 30 minutes followed by filtering through Celite. The filtrate was extracted with ether. The organic layers was washed with saturated aqueous sodium bicarbonate and saturated brine and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled away under a reduced pressure. The resultant residue was purified by column chromatography on silica gel (hexane: ethyl acetate=4:1) to obtain methyl 4-phenyl-2-indancarboxylate. The resultant ester was dissolved in methanol to which 1 N sodium hydroxide was added to hydrolyze. Methanol was distilled away under a reduced pressure. To the resultant residue was added 1 N hydrochloric acid. The product was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled away to obtain the title compound (351 mg) (melting point: 97-102° C.).

Workup

  1. additionwas added
  2. distillationMethanol was distilled away under a reduced pressure
  3. additionTo the resultant residue was added 1 N hydrochloric acid
  4. extractionThe product was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, the solvent was distilled away

Sources & evidence

ORD record
ord-82694969b5b3470bb39ad50f950258ee
Source dataset
uspto-grants-2000_05
Patent number
US06057335

Reaction notes

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