Water → 2-(3-Fluorophenyl)cyclopropanecarboxylic acid

HRID 857013Notes

Reaction equation

HRID 857013 reaction equation
CON(C)[C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)=[O:5].[OH2:17].[OH-].[Na+]>CO>[F:15][C:11]1[CH:10]=[C:9]([CH:7]2[CH2:8][CH:6]2[C:4]([OH:17])=[O:5])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 587594712-(3-Fluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide

Product 1

HCID 218646592-(3-Fluorophenyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(3-fluoro-phenyl)-cyclopropanecarboxylic acid methoxy-methyl-amide (8.96 g), water (20 mL), and NaOH (3.2 g) in MeOH (40 mL) was refluxed for 3 h. The reaction mixture was cooled down to room temperature and concentrated in vacuo. The residue was acidified by 6 N HCl followed by extraction with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (7.1 g).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationconcentrated in vacuo
  3. extractionfollowed by extraction with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6d4d52d97924abb9485e63f1c935f21
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

Loading…