Nitromethane → 2-Benzyloxy-4-isopropyl-1-(2-nitrovinyl)benzene

HRID 1272408Notes

Reaction equation

HRID 1272408 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][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+:25]([CH3:28])([O-:27])=[O:26]>>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=[CH:28][N+:25]([O-:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 178562862-Benzyloxy-4-isopropylbenzaldehyde

Product 1

HCID 688252572-Benzyloxy-4-isopropyl-1-(2-nitrovinyl)benzene

Conditions

Temperature
100 °C

Procedure

To 100 mL of nitromethane were added 10.44 g of 2-benzyloxy-4-isopropylbenzaldehyde and 4.71 g of ammonium acetate. After being stirred at external 100° C. for 3 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and the organic layer was washed successively with 1 mol/L hydrochloric acid, and saturated aqueous sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 9.45 g of 2-benzyloxy-4-isopropyl-1-(2-nitrovinyl)benzene.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethyl acetate
  3. washthe organic layer was washed successively with 1 mol/L hydrochloric acid, and saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ba480470ff1e40fc93480c231ecf4109
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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