Methanol → Methyl indane-2-carboxylate

HRID 2215092Notes

Reaction equation

HRID 2215092 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].OS(O)(=O)=O.[CH3:18]O>>[CH3:18][O:11][C:10]([CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5757772-Indancarboxylic Acid

Product 1

HCID 9964238Methyl indane-2-carboxylateYield 95%

Procedure

Indan-2-carboxylic acid (2.0 g, 12.34 mmol) was dissolved in MeOH (50 mL) and was then treated with H2SO4 (1 mL). The reaction mixture was refluxed overnight. MeOH was evaporated and the residue was diluted with water and ether. Layers were separated and the aqueous layer was extracted with ether (2×30 mL). The combined organics were dried with MgSO4 and condensed to afford the product (2.01 g, 95%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customMeOH was evaporated
  3. additionthe residue was diluted with water and ether
  4. customLayers were separated
  5. extractionthe aqueous layer was extracted with ether (2×30 mL)
  6. dry with materialThe combined organics were dried with MgSO4 and condensed

Sources & evidence

ORD record
ord-7ace3ef2a9f14934bafc67514095f926
Source dataset
uspto-grants-2006_09
Patent number
US07109222B2

Reaction notes

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