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

HRID 1514204Notes

Reaction equation

HRID 1514204 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 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-methylethyl 4-[(1-methylethyl)oxy]-3-(trifluoromethyl)benzoate (Preparation 38) (3.63 g, 12.5 mmol) in ethanol (100 ml) was added aqueous sodium hydroxide (12.5 M, 10.0 ml, 125 mmol) and the reaction heated to reflux for 3 hrs. The mixture was concentrated in vacuo and the residue partitioned between EtOAc (100 ml) and water (100 ml) and acidified with aqueous hydrochloric acid. The aqueous layer was extracted further with EtOAc (100 ml) and the combined organic layers dried and concentrated in vacuo to give the title compound as a yellow solid (2.68 g, 10.8 mmol). MS (ES−): C11H11F3O3 requires 248; found 247 [M−H+].

Workup

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

Sources & evidence

ORD record
ord-d03a60ba8b2f4e5491e040eff2637b0e
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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