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

HRID 78278
Notes
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Reaction equation

HRID 78278 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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-4245e0c393014aae9eda696d8b07c9f8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841327B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes