Methyl iodide → Methyl 1-(4-fluorophenyl)-4-oxocyclohexane-1-carboxylate

HRID 1065264Notes

Reaction equation

HRID 1065264 reaction equation
[CH3:1][O-].[Na+].[Na].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:19]([OH:21])=[O:20])[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.IC>CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:19]([O:21][CH3:1])=[O:20])[CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17]2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

Product 1

HCID 20540244Methyl 1-(4-fluorophenyl)-4-oxocyclohexane-1-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred sodium methoxide solution, previously prepared starting from 1.3 parts of sodium in 160 parts of methanol, are added 13 parts of 1-(4-fluorophenyl)-4-oxocyclohexanecarboxylic acid and the whole is stirred and refluxed for 1 hour. After cooling to room temperature, 22.8 parts of iodomethane are added dropwise. Upon completion, the whole is heated to reflux and stirring is continued overnight at reflux temperature. The reaction mixture is evaporated and the residue is taken up in trichloromethane. The organic phase is washed successively with water, a 5% sodium hydroxide solution and again with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5 parts (36%) of methyl 1-(4-fluorophenyl)-4-oxocyclohexanecarboxylate as an oily residue.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureUpon completion, the whole is heated
  3. temperatureto reflux
  4. stirringstirring
  5. temperatureat reflux temperature
  6. customThe reaction mixture is evaporated
  7. washThe organic phase is washed successively with water
  8. dry with materiala 5% sodium hydroxide solution and again with water, dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is purified by column-chromatography over silica gel
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

Sources & evidence

ORD record
ord-38035ee2605541f28c7ce94a77de033b
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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