Sulfuric Acid → Methyl 1-(3-fluorophenyl)cyclopentanecarboxylate

HRID 28770Notes

Reaction equation

HRID 28770 reaction equation
C[CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[C:22](=O)([O-])[O-].[Na+].[Na+]>CO>[F:16][C:12]1[CH:11]=[C:10]([C:3]2([C:7]([O:9][CH3:22])=[O:8])[CH2:4][CH2:5][CH2:6][CH2:2]2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 69250637HCID 69250637, compound

Product 1

HCID 20110264Methyl 1-(3-fluorophenyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(3-fluorophenyl)cyclopentanecarboxylic acid (5.0 g, 24.01 mmol) in anhydrous methanol was added 1 mL of concentrated sulfuric acid. The mixture was refluxed overnight. The mixture was neutralized to pH 4-5 with sodium carbonate. The solvent was evaporated. The residue was dissolved in ethyl acetate (50 mL), washed with brine (3×10 mL, dried over MgSO4. The crude product was used for the next reaction without further purification.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washwashed with brine (3×10 mL
  5. dry with materialdried over MgSO4
  6. customThe crude product was used for the next reaction without further purification

Sources & evidence

ORD record
ord-85a51530157c465491b5ec841d9f72cc
Source dataset
uspto-grants-2008_09
Patent number
US07419999B2

Reaction notes

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