Nitromethane → 2-n-Hexyl-3-nitromethylcyclopentanone

HRID 328059Notes

Reaction equation

HRID 328059 reaction equation
[CH2:1]([C:7]1[C:8](=[O:12])[CH2:9][CH2:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N+:13]([CH3:16])([O-:15])=[O:14].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[CH2:1]([CH:7]1[CH:11]([CH2:16][N+:13]([O-:15])=[O:14])[CH2:10][CH2:9][C:8]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 667682-Hexyl-2-cyclopenten-1-oneHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 214437372-n-Hexyl-3-nitromethylcyclopentanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 2-L flask fitted with a reflux condenser, is placed 332 g of 2-n-hexyl-2-cyclopentenone, 183 g of nitromethane, 30 ml of 40% methanolic solution of benzyltrimethylammonium hydroxide (Triton B) and 200 ml of dry dioxane. The reaction mixture is refluxed for 23 hours. The solvent is distilled off under a reduced pressure and the residue is dissolved in 1 L of ether. The ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution and dried over anhydrous sodium sulphate. The solvent is removed at atmospheric pressure and the residue is distilled through a short Vigreux column. After a lower boiling fraction (35 g, 65° C/0.2 mm) consisting of 2-n-hexyl-2-cyclopentenone, the product is collected at 135° C/0.3 mm, yield 365 g (80%), nD20 1.4733.

Workup

  1. customIn a 2-L flask fitted with a reflux condenser
  2. temperatureThe reaction mixture is refluxed for 23 hours
  3. distillationThe solvent is distilled off under a reduced pressure
  4. dissolutionthe residue is dissolved in 1 L of ether
  5. washThe ether solution is washed successively with dilute hydrochloric acid, water and sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent is removed at atmospheric pressure
  8. distillationthe residue is distilled through a short Vigreux column
  9. customAfter a lower boiling fraction (35 g, 65° C/0.2 mm)
  10. customthe product is collected at 135° C/0.3 mm, yield 365 g (80%)

Sources & evidence

ORD record
ord-efbadcba02dd41b886da66b6e6c9c1d4
Source dataset
uspto-grants-1977_04
Patent number
US04016109

Reaction notes

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