Sodium Hydroxide → HCID 68722114, compound

HRID 577466Notes

Reaction equation

HRID 577466 reaction equation
[CH3:1][C:2]1[C:13]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[C:13]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86723696HCID 86723696, compound

Product 1

HCID 68722114HCID 68722114, compoundYield 122.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of propan-2-yl 2-methyl-3-(propan-2-yloxy)benzoate (Cpd MM, 3.97 g, 16.8 mmol) in THF (40 mL) was added 2N NaOH (25.2 mL, 50.4 mmol). The reaction mixture turned light yellow and was heated at 65° C. for 3 days. The reaction mixture was cooled to room temperature, then concentrated under vacuum. The residue was acidified with 10% HCl (aq) then extracted with EtOAc. The organic layer was washed with brine, dried with Na2SO4 then concentrated under vacuum to give 2-methyl-3-(propan-2-yloxy)benzoic acid (Cpd NN, 4.0 g, 100%) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. extractionthen extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-76c8c39f52904bb3b74fb3f936ee4da0
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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