Lithium Hydroxide → HCID 89580924, compound

HRID 1501210Notes

Reaction equation

HRID 1501210 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:13]=[C:12]([CH:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:15])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>O1CCCC1.C1(C)CCC(C(C)C)C(O)C1.O>[F:3][C:4]1[CH:13]=[C:12]([CH:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:15])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 89581031HCID 89581031, compound

Product 1

HCID 89580924HCID 89580924, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1254MentholSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Lithium hydroxide (420 mg, 10.2 mmol) in tetrahydrofuran, menthol and water (20 mL, 3:1:1, V/V) was added methyl 2-fluoro-4-(1-phenoxyethyl)benzoate (600 mg, 2.42 mmol). The reaction mixture was stirred at room temperature for 1 h. The mixture was quench with 10% hydrochloric acid (aqueous), extracted with dichloromethane and menthol (30 mL, 10:1), the combine organic layer was dried with anhydrous sodium sulfate, filtered and evaporated to give product 2-fluoro-4-(1-phenoxyethyl)benzoic acid (450 mg, 82%). LCMS (M+H+) m/z: calcd 260.08. found 260.

Workup

  1. customThe mixture was quench with 10% hydrochloric acid (aqueous)
  2. extractionextracted with dichloromethane and menthol (30 mL, 10:1)
  3. dry with materialthe combine organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4479adaf894a430690a3c1fd87ad2ab3
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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