Nitromethane → 1-(Benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene

HRID 1173333Notes

Reaction equation

HRID 1173333 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[C:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:30]([CH3:33])([O-:32])=[O:31]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[C:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:10]=1[CH:11]=[CH:33][N+:30]([O-:32])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 866011722-(Benzyloxy)-4,6-di-tert-butylbenzaldehyde

Product 1

HCID 687177311-(Benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1.5 g (4.6 mmol) of the product of Step A and 2.0 g of ammonium acetate in 25 mL acetic acid was added 3 mL nitromethane. The reaction mixture was refluxed for 5 h, then cooled to room temperature and the volatiles were removed in vacuo. The residue was partitioned between EtOAc and water, then separated. The aqueous layer was re-extracted with EtOAc, the organic layers were combined, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 0-20% CH2Cl2-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customthe volatiles were removed in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. customseparated
  5. extractionThe aqueous layer was re-extracted with EtOAc
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 0-20% CH2Cl2-hexane
  11. customCombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-e3f1b22b518f4e479d5ca5b9ad9cedc6
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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