Methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate → Methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

HRID 547665Notes

Reaction equation

HRID 547665 reaction equation
[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[H][H]>C(O)(=O)C.OS(O)(=O)=O>[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 12522314Methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57565328Methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of the methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (2.04 g, 9.99 mmol) in glacial acetic acid (22 mL) and concentrated H2SO4 (2 mL) was hydrogenated on a Parr apparatus under 50 psi of hydrogen using 10% palladium on carbon (50% H2O, 0.200 g) as the catalyst. After 4 hours the reaction was filtered to remove the catalyst and washed 2× methanol, then concentrated to remove most of the acetic acid. The residue was neutralized using saturated Na2CO3 and the organics extracted twice with 25 mL ethyl acetate, then the combined organics washed with brine, dried (Na2SO4), filtered and concentrated to 2.0 g of methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate.

Workup

  1. filtrationAfter 4 hours the reaction was filtered
  2. customto remove the catalyst
  3. washwashed 2× methanol
  4. concentrationconcentrated
  5. customto remove most of the acetic acid
  6. extractionthe organics extracted twice with 25 mL ethyl acetate
  7. washthe combined organics washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated to 2.0 g of methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Sources & evidence

ORD record
ord-51d3487e014240dba915a8efcdb4f4a2
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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