Lithium Hydroxide → 4-(3-(Trifluoromethoxy)benzyl)benzoic acid

HRID 2359325Notes

Reaction equation

HRID 2359325 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]([F:22])([F:23])[O:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH2:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58046326Ethyl 4-[3-(trifluoromethoxy)benzyl]benzoate

Product 1

HCID 580463074-(3-(Trifluoromethoxy)benzyl)benzoic acidYield 69.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 4-[3-(trifluoromethoxy)benzyl]benzoate (Preparation 149, 950 mg, 2.93 mmol) in THF/MeOH/water (4:3:2, 27 mL) was added lithium hydroxide (246 mg, 5.86 mmol) and the mixture was stirred at room temperature for 4 hours. The mixture was concentrated in vacuo and acidified with 1M hydrochloric acid solution. The resulting precipitate was filtered off and dried to give the title compound as a white solid (600 mg, 69%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried

Sources & evidence

ORD record
ord-9a150421cd054e068ae8b5f1f0f0f8a2
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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