Nitromethane → 1-Ethyl-2-(2-nitroethyl)benzene

HRID 20431Notes

Reaction equation

HRID 20431 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O)[CH3:2].[N+:11]([CH3:14])([O-:13])=[O:12].C([O-])(=O)C.[NH4+].[BH4-].[Na+]>C(O)(=O)C>[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][CH2:14][N+:11]([O-:13])=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 1234062-EthylbenzaldehydeHCID 517165Ammonium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 685580161-Ethyl-2-(2-nitroethyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve 2-ethyl benzaldehyde (7 mL, 53.2 mmol), nitromethane (8.5 mL, 158 mmol), and ammonium acetate (1.6 g, 20.8 mmol) in acetic acid (40 mL) and heat to reflux under a nitrogen atmosphere for 17 hours. Cool to room temperature and concentrate. Dissolve in isopropyl alcohol (150 mL) and chloroform (750 mL) and add silica gel (108 g). To the resulting slurry, slowly add sodium borohydride (7.8 g, 206 mmol). Stir the mixture for 17 hours, filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes), to give the desired compound as an orange oil.

Workup

  1. temperatureheat
  2. temperatureto reflux under a nitrogen atmosphere for 17 hours
  3. concentrationconcentrate
  4. dissolutionDissolve in isopropyl alcohol (150 mL)
  5. additionchloroform (750 mL) and add silica gel (108 g)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-4702e875061b4cd8b30bacc08984ca33
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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