alpha-Chloro-m-nitrotoluene → 1-(Methoxymethyl)-3-nitrobenzene

HRID 1702515Notes

Reaction equation

HRID 1702515 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 12078alpha-Chloro-m-nitrotolueneHCID 10942334Sodium Methoxide

Product 1

HCID 113896091-(Methoxymethyl)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500-milliliter flask equipped with a reflux condenser and a magnetic stirring bar was charged with 17.1 grams (0.1 mole) of 3-nitrobenzyl chloride in 200 milliliters of methanol. To this stirred solution was added 10.8 grams (0.2 mole) of sodium methoxide. Exothermic heating was observed. The reaction mixture was heated to reflux and maintained at reflux for 22 hours. The reaction mixture was then cooled, filtered, and the filtrate was transferred to a separatory funnel wherein it was diluted with 400 milliliters of ethyl acetate and consecutively extracted with 400 milliliters of water and 400 milliliters of saturated brine respectively. The organic phase was separated, dried over magnesium sulfate, and concentrated on a rotary evaporator at 55° C., leaving a brown liquid. The brown liquid was charged to a distillation flask and distilled at a pressure of 2.3 millimeters of mercury. A main fraction (15.1 grams) was collected, said fraction having a boiling point of 118°-120° C. at 2.3 mm Hg pressure. This main fraction was identified by NMR spectroscopy as 1-(methoxymethyl)-3-nitrobenzene.

Workup

  1. customA 500-milliliter flask equipped with a reflux condenser and a magnetic stirring bar
  2. temperatureExothermic heating
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. temperatureat reflux for 22 hours
  7. temperatureThe reaction mixture was then cooled
  8. filtrationfiltered
  9. customthe filtrate was transferred to a separatory funnel
  10. additionwherein it was diluted with 400 milliliters of ethyl acetate
  11. extractionconsecutively extracted with 400 milliliters of water and 400 milliliters of saturated brine respectively
  12. customThe organic phase was separated
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated on a rotary evaporator at 55° C.
  15. customleaving a brown liquid
  16. additionThe brown liquid was charged to a distillation flask
  17. distillationdistilled at a pressure of 2.3 millimeters of mercury
  18. customA main fraction (15.1 grams) was collected

Sources & evidence

ORD record
ord-78c3ff7e7bbf4614b690ad564cf6162c
Source dataset
uspto-grants-1982_09
Patent number
US04348223

Reaction notes

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