1,5-Diiodopentane → 1-(4-Chlorobenzoyl)cyclohexaneacetic acid

HRID 1953267Notes

Reaction equation

HRID 1953267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]I>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]2([CH2:10][C:11]([OH:13])=[O:12])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 123541,5-DiiodopentaneHCID 24758Sodium hydrideHCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 184123331-(4-Chlorobenzoyl)cyclohexaneacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.4 g (0.04 mol) of 4-(4-chlorophenyl)-4-oxo-butyric acid are dissolved in 300 ml tetrahydrofuran, combined batchwise with 5.8 g (0.12 mol) of sodium hydride (50% in oil) and refluxed for 90 minutes. After the addition of 8.9 ml (0.06 mol) of 1,5-diiodopentane the reaction mixture is refluxed for a further 3 hours. After cooling the reaction mixture is stirred into ice water, the tetrahydrofuran is distilled off and the residue is extracted with methylene chloride. The aqueous phase is acidified with hydrochloric acid and extracted with methylene chloride. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with methylene chloride+ethanol (1 to 2%).

Workup

  1. temperaturerefluxed for 90 minutes
  2. temperatureis refluxed for a further 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. distillationthe tetrahydrofuran is distilled off
  5. extractionthe residue is extracted with methylene chloride
  6. extractionextracted with methylene chloride
  7. customThe combined organic extracts are dried
  8. customevaporated down
  9. customThe residue is chromatographed on silica gel
  10. washeluted with methylene chloride+ethanol (1 to 2%)

Sources & evidence

ORD record
ord-02094331da6f4203be8ab35ef61e3955
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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