Sulfuric Acid → 1,3-Dimethyl-1H-indene-2-carboxylic acid

HRID 19720Notes

Reaction equation

HRID 19720 reaction equation
S(=O)(=O)(O)O.[C:6]([CH:9]([CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:10]([O:12]C)=[O:11])(=O)[CH3:7]>>[CH3:7][CH:6]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]([CH3:15])=[C:9]1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 12561390Methyl 2-acetyl-3-phenylbutyrate

Product 1

HCID 566300951,3-Dimethyl-1H-indene-2-carboxylic acid

Procedure

Concentrated sulphuric acid (15 ml) is added to methyl 2-acetyl-3-phenylbutyrate (2.75 g, 12.5 mmol) maintaining the temperature below 30° C. The reaction is stirred at ambient temperature for 5 hours, poured on to ice and extracted with EtOAc. The combined organic extracts are evaporated and the residue is diluted with water and the pH adjusted to 8 with saturated NaHCO3. After washing with EtOAc, the aqueous phase is acidified with concentrated HCl and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated to afford the title compound, MH+189.

Workup

  1. temperaturemaintaining the temperature below 30° C
  2. additionpoured on to ice
  3. extractionextracted with EtOAc
  4. customThe combined organic extracts are evaporated
  5. additionthe residue is diluted with water
  6. washAfter washing with EtOAc
  7. extractionextracted with EtOAc
  8. washThe combined organic phases are washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-4529735b5d0c49b1bacdc6b2fd11d5d9
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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