Hydrochloric Acid → 2-methyl-2,3-dihydro-1H-indene-2-carboxylic acid

HRID 547666Notes

Reaction equation

HRID 547666 reaction equation
[CH3:1][C:2]1([C:11]([O:13]C)=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.O.[OH-].[Li+].Cl>O1CCCC1.O.CO>[CH3:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57565328Methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 153388422-methyl-2,3-dihydro-1H-indene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a tetrahydrofuran/H2O/methanol (4 mL/1 mL/1 mL) solution of the methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate (1.80 g, 9.46 mmol) was added lithium hydroxide monohydrate (1.19 g, 28.39 mmol). The reaction mixture stirred at ambient temperature for 4 hours and then the mixture was acidified to pH 3 using 1N HCl. The organics were extracted twice with 25 mL diethyl ether, the combined organics were washed with brine and then dried (Na2SO4), filtered and concentrated to as 2-Methyl-2,3-dihydro-1H-indene-2-carboxylic acid a white solid.

Workup

  1. extractionThe organics were extracted twice with 25 mL diethyl ether
  2. washthe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to as 2-Methyl-2,3-dihydro-1H-indene-2-carboxylic acid a white solid

Sources & evidence

ORD record
ord-72939a34af194ea6bd9e8ebb24592bb4
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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