Sulfuric Acid → Methyl indane-2-carboxylate

HRID 261924Notes

Reaction equation

HRID 261924 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[C:18](=O)(O)[O-].[Na+]>CO>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:10]([O:12][CH3:18])=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5757772-Indancarboxylic Acid

Product 1

HCID 9964238Methyl indane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50 g. of indan-2-carboxylic acid (prepared according to the procedure reported by E. D. Bergmann and E. Hoffman, J. Org. Chem., 26, 3555 (1961)) and 5 ml. of con d sulfuric acid in 500 ml. of methanol is heated at reflux for 3.0 hours then is cooled in ice. The cooled solution is neutralized (pH~5) with saturated sodium bicarbonate, is concentrated, and the aqueous layer is extracted with methylene chloride. The combined organic extracts are washed with saturated bicarbonate, with saturated brine, are dried (anhydrous magnesium sulfate), and are concentrated. Distillation of the crude residue in vacuo provides the desired methyl indan-2-carboxylate.

Workup

  1. temperatureat reflux for 3.0 hours
  2. temperaturethen is cooled in ice
  3. concentrationis concentrated
  4. extractionthe aqueous layer is extracted with methylene chloride
  5. washThe combined organic extracts are washed with saturated bicarbonate, with saturated brine
  6. dry with materialare dried (anhydrous magnesium sulfate)
  7. concentrationare concentrated
  8. distillationDistillation of the crude residue in vacuo

Sources & evidence

ORD record
ord-7fc766a363da4687a61b33b11bdc0416
Source dataset
uspto-grants-1979_05
Patent number
US04152527

Reaction notes

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