Sodium Hydroxide → 4-Isopropoxy-3-(trifluoromethyl)benzoic acid

HRID 2189768Notes

Reaction equation

HRID 2189768 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:16]=[CH:15][C:8]([C:9]([O:11]C(C)C)=[O:10])=[CH:7][C:6]=1[C:17]([F:20])([F:19])[F:18])[CH3:3].[OH-].[Na+]>C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:16]=[CH:15][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[C:17]([F:18])([F:20])[F:19])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59201795Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

Product 1

HCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-methylethyl 4-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzoate (D35) (704 mg, 2.43 mmol) in ethanol (110 mL) was added aqueous sodium hydroxide (2M, 12.2 mL, 24.3 mmol) and the reaction heated to reflux for 1 h. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL) and acidified with aqueous hydrochloric acid (2M, 13 mL). The aqueous layer was extracted further with ethyl acetate (100 mL) and the combined organic layers dried and concentrated in vacuo to give the title compound as a yellow solid (563 mg). MS (ES): C11H11F3O3 requires 248; found 247 (M−H+).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 1 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  5. extractionThe aqueous layer was extracted further with ethyl acetate (100 mL)
  6. customthe combined organic layers dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d73d5942489d492188e6e8ae0879bfae
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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