Sodium Methoxide → 1-Ethyl-2-(methoxymethyl)-4-nitrobenzene

HRID 261293Notes

Reaction equation

HRID 261293 reaction equation
[CH3:1][O-:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[CH2:15][CH3:16]>CO>[CH3:1][O:2][CH2:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 123759392-(Chloromethyl)-1-ethyl-4-nitrobenzene

Product 1

HCID 1165461-Ethyl-2-(methoxymethyl)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
3 °C

Procedure

Sodium methoxide is added portionwise to a solution of 150.0 g of α-chloro-2-ethyl-5-nitrotoluene in 1.15 l. of methanol maintained between 18° C. and 30° C. The mixture is refluxed for 2 hours, cooled to 3° C., and filtered. The filtrate is concentrated under vacuum and the resulting slurry shaken with saturated aqueous sodium chloride and methylene chloride. The methylene chloride layer is washed, filtered through sodium sulfate, and stirred over magnesium sulfate. The filtered solution is concentrated under vacuum to yield 133.89 g. of a dark brown liquid. The crude product is fractionated by vacuum distillation to yield a yellow liquid with boiling point 113° C. to 115° C. at 0.35 mm Hg which solidifies to light yellow prisms with mp 21.5° C. to 23.5° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under vacuum
  4. washThe methylene chloride layer is washed
  5. filtrationfiltered through sodium sulfate
  6. stirringstirred over magnesium sulfate
  7. concentrationThe filtered solution is concentrated under vacuum
  8. customto yield 133.89 g
  9. distillationThe crude product is fractionated by vacuum distillation
  10. customto yield a yellow liquid with boiling point 113° C. to 115° C. at 0.35 mm Hg which

Sources & evidence

ORD record
ord-eea03b38fd374c4da1de0f0c8bee0bb8
Source dataset
uspto-grants-1979_08
Patent number
US04165231

Reaction notes

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