Methanol → 2-(2-Fluorophenyl)cyclopropane-1-carboxylic acid

HRID 1351590Notes

Reaction equation

HRID 1351590 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[C:11]([O:13]C)=[O:12].[OH-].[Na+].O.CO>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][CH:9]1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 22135583Methyl 2-(2-fluorophenyl)cyclopropanecarboxylate

Product 1

HCID 218646742-(2-Fluorophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2-fluorophenyl)cyclopropanecarboxylate (4.8 g, 24.72 mmol) in tetrahydrofuran (25 mL), was added 10M sodium hydroxide solution (approximately 2 mL), a small amount of water, and sufficient methanol to achieve a homogeneous reaction mixture. The reaction mixture was then allowed to stir at rt for approximately 2 h. After concentrating the reaction mixture, 1N HCl was added until the mixture was acidic. The organic layer was extracted twice with ethyl acetate, then washed with brine, dried over anhydrous Na2SO4, and concentrated to afford the title compound. M.S. (M+1): 181.

Workup

  1. concentrationAfter concentrating the reaction mixture, 1N HCl
  2. additionwas added until the mixture
  3. extractionThe organic layer was extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-027868c44ee84b76a7910ba739a47687
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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