Sulfuric Acid → Methyl indane-2-carboxylate

HRID 375544Notes

Reaction equation

HRID 375544 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].[CH3:13]OC(OC)(C)C.S(=O)(=O)(O)O>CO>[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][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 5757772-Indancarboxylic Acid

Product 1

HCID 9964238Methyl indane-2-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 2-indancarboxylic acid (3.82 g, 23.5 mmol) in methanol (60 mL) and treat with dimethoxypropane (5.8 mL, 47 mmol) and sulfuric acid (0.8 mL). Stir at room temperature for 6 days. Evaporate the solvent in vacuo, dilute with methylene chloride (75 mL) and wash with saturated sodium hydrogen carbonate (35 mL). Extract the aqueous phase with methylene chloride (30 mL), wash combined organics with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and pass through a plug of silica gel to give 2-(carbomethoxy)indan as a yellow oil (3.98 g).

Workup

  1. customEvaporate the solvent in vacuo
  2. additiondilute with methylene chloride (75 mL)
  3. washwash with saturated sodium hydrogen carbonate (35 mL)
  4. extractionExtract the aqueous phase with methylene chloride (30 mL)
  5. washwash
  6. dry with materialdry (Na2SO4)
  7. customEvaporate the solvent in vacuo and pass through a plug of silica gel

Sources & evidence

ORD record
ord-fc9f448240444ee1a20b4d6e0edafc5f
Source dataset
uspto-grants-1996_01
Patent number
US05486513

Reaction notes

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