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Nitromethane → (E)-2-(Benzyloxy)-1-(2-ethoxyethoxy)-4-(2-nitrovinyl)benzene

HRID 1427036
Notes
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Reaction equation

HRID 1427036 reaction equation
C([O-])(=O)C.[NH4+].[N+:6]([CH3:9])([O-:8])=[O:7].[CH2:10]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])[CH:21]=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C>[CH2:10]([O:17][C:18]1[CH:19]=[C:20](/[CH:21]=[CH:9]/[N+:6]([O-:8])=[O:7])[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 86730338HCID 86730338, compound

Product 1

HCID 86730339(E)-2-(Benzyloxy)-1-(2-ethoxyethoxy)-4-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

Ammonium acetate (4.16 g, 53.9 mmol) and nitromethane (6.1 mL, 113 mmol) were added to a solution of 3-(benzyloxy)-4-(2-ethoxyethoxy)benzaldehyde described in Production Example 24-2 (13.5 g, 45.0 mmol) in acetic acid (36 mL) under nitrogen atmosphere at room temperature. The liquid mixture was heated and stirred under reflux at 130° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature. The precipitate was collected by filteration and washed with ethanol to quantitatively obtain the title compound.

Workup

  1. temperatureThe liquid mixture was heated
  2. customThe reaction liquid
  3. temperatureto cool to room temperature
  4. customThe precipitate was collected by filteration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-eced5d020db44afe87b27b41de7fd1a4
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes