Acetic Acid → (E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzene

HRID 1694232Notes

Reaction equation

HRID 1694232 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[N+:21]([CH3:24])([O-:23])=[O:22].C([O-])(=O)C.[NH4+]>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:24]/[N+:21]([O-:23])=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 517165Ammonium Acetate

Product 1

HCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-benzyloxy benzaldehyde (50 g, 0.24 mol) and acetic acid (200 mL) were added nitromethane (64 mL, 1.2 mol) and ammonium acetate (36 g, 0.47 mol), which was stirred for 90 minutes at 100° C. The reaction mixture was cooled to room temperature, and water (1 L) was added at the same temperature. The deposited solids were filtered to obtain the title compound (60 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe deposited solids were filtered

Sources & evidence

ORD record
ord-f4938501f7d84796847f3b088a90b752
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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