Nitromethane → Sodium 2-nitro-1-(4-phenoxy-phenyl)ethanolate

HRID 77838Notes

Reaction equation

HRID 77838 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+:18].[N+:19]([CH3:22])([O-:21])=[O:20]>CO>[N+:19]([CH2:22][CH:12]([C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1)[O-:13])([O-:21])=[O:20].[Na+:18]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 661394-PhenoxybenzaldehydeHCID 10942334Sodium Methoxide2×

Product 1

HCID 66707614Sodium 2-nitro-1-(4-phenoxy-phenyl)ethanolateYield 457.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-phenoxybenzaldehyde (1.5 g, 7.56 mmol) in methanol (12 mL) was added dropwise sodium methoxide (1.49 M methanol solution, 0.19 mL, 0.91 mmol) under nitrogen atmosphere at room temperature. Nitromethane (530 μL, 9.84 mmol) was added dropwise to the reaction solution on an ice bath (0° C.). Sodium methoxide (1.49 M methanol solution, 1.66 mL, 8.16 mmol) was added dropwise thereto at room temperature, and the solution was stirred for 30 minutes at room temperature. The precipitated solids were filtered and dried under reduced pressure, and the solids were dried azeotropically with toluene to obtain the title compound (1.17 g, 55%).

Workup

  1. filtrationThe precipitated solids were filtered
  2. customdried under reduced pressure
  3. dry with materialthe solids were dried azeotropically with toluene

Sources & evidence

ORD record
ord-bd2d18aa44914a61befe134080350024
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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