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

HRID 70279Notes

Reaction equation

HRID 70279 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>C1COCC1.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 solution of methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate (1.80 g, 9.46 mmol) in THF/water/MeOH (4/1/1 mL respectively) was added lithium hydroxide monohydrate (1.19 g, 28.4 mmol). The reaction mixture stirred at ambient temperature 4 h, acidified to pH 3 with 1 N HCl and extracted with Et2O (2×25 mL). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.39 (s, 3H), 2.83 (d, J=15.9 Hz, 2 H), 3.50 (d, J=15.9 Hz, 2 H), 7.12-7.23 (m, 4H).

Workup

  1. extractionextracted with Et2O (2×25 mL)
  2. washCombined organics were washed (water, brine)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92969a4d7d6d45f58dd49a4b4cbc2d84
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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