Nitromethane → (1-Nitromethylcyclohexyl)acetic acid ethyl ester

HRID 724493Notes

Reaction equation

HRID 724493 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]=[C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:2].[N+:13]([CH3:16])([O-:15])=[O:14].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1([CH2:16][N+:13]([O-:15])=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 73776Ethyl cyclohexylideneacetateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 11128083(1-Nitromethylcyclohexyl)acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

14.8 g (0.088 mol) of the cyclohexylideneacetic acid ethyl ester produced according to 1.1 were dissolved in 50 ml of tetrahydrofuran, 7.11 ml (0.132 mol) of nitromethane and 88 ml of tetrabutylammonium fluoride (1 molar in tetrahydrofuran) were added under a nitrogen atmosphere and refluxed for 20 hours. After cooling, the mixture was diluted with 50 ml of water and extracted three times with dieethyl ether. The organic phase was washed with 10 wt. % aqueous potassium hydrogensulfate solution and then washed with water, dried over magnesium sulfate and evaporated. (1-Nitromethylcyclohexyl)acetic acid ethyl ester was obtained as an orange-yellow oily liquid. The yield amounted to 19.8 g (98% of theoretical).

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureAfter cooling
  3. extractionextracted three times with dieethyl ether
  4. washThe organic phase was washed with 10 wt. % aqueous potassium hydrogensulfate solution
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-5f526019b12845bfbeb43cdc56df922f
Source dataset
uspto-grants-2006_11
Patent number
US07141695B2

Reaction notes

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