Lithium Hydroxide → HCID 89581389, compound

HRID 1501203Notes

Reaction equation

HRID 1501203 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])[C:5]([O:7]C)=[O:6].[OH-].[Li+]>O1CCCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 89581073HCID 89581073, compound

Product 1

HCID 89581389HCID 89581389, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 3-fluoro-4-(1-phenoxyethyl)benzoate (400 mg, 1.5 mmol) in mixed solution of tetrahydrofuran/methanol/water=3:1:1 (4 mL) was added lithium hydroxide (200 mg, 8.4 mmol). The mixture was stirred at room temperature for 2 hours. The suspension was concentrated in vacuo and quenched with hydrochloride acid aqueous (1N, 5 mL). To the residue, water (50 mL) was added and extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give 3-fluoro-4-(1-phenoxyethyl)benzoic acid as pale solid (300 mg, 82%).

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. customquenched with hydrochloride acid aqueous (1N, 5 mL)
  3. additionTo the residue, water (50 mL) was added
  4. extractionextracted with dichloromethane (2*50 mL)
  5. customThe combined organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0324b1b81a2845eda98e20e87f53ecb9
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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