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

HRID 423346Notes

Reaction equation

HRID 423346 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 (D70) (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). δH (methanol-d4, 400 MHz): 8.21-8.17 (2H, m), 7.26 (1H, d), 4.84 (1H, septet), 1.38 (6H, d). 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-835cfce251f343068f3b0c13724f7599
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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