Sodium Methoxide → HCID 13042037, compound

HRID 1702519Notes

Reaction equation

HRID 1702519 reaction equation
[CH3:1][CH:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:1]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 130351521-(1-Chloroethyl)-3-nitrobenzene2×

Product 1

HCID 13042037HCID 13042037, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1,000-milliliter flask equipped with a reflux condenser and a magnetic stirring bar was charged with 24.1 grams (0.13 mole) of α-methyl-3-nitrobenzyl chloride in 400 milliliters of methyl alcohol. To this stirred solution was added 8.1 grams (0.15 mole) of sodium methoxide. The reaction mixture was heated to reflux and maintained at reflux for 26 hours. Since some traces of α-methyl-3-nitrobenzyl chloride were present (as indicated by a thin layer chromatograph test), an additional 5.4 grams (0.1 mole) of sodium methoxide was added and the reaction was again heated to reflux and maintained at reflux for 49 hours. The reaction mixture was then cooled and concentrated on a rotary evaporator at 55° C. The residue was taken up with 200 milliliters of methylene chloride, transferred to a separatory funnel and washed consecutively with 100 milliliter portions each of water, 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water, respectively. The organic layer was separated, dried over magnesium sulfate and concentrated on a rotary evaporator at 55° C., leaving a dark liquid residue. The dark liquid was charged to a distillation flask and distilled at a pressure of 1.8 millimeters of mercury. A main fraction (14.98 grams) was collected, said fraction having a boiling point of 106° C.-112° C. at 1.8 mm Hg pressure. This main fraction was identified by NMR spectroscopy as 1-(1-methoxyeth-1-yl)-3-nitrobenzene.

Workup

  1. customA 1,000-milliliter flask equipped with a reflux condenser and a magnetic stirring bar
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for 26 hours
  6. additionwas added
  7. temperaturethe reaction was again heated
  8. temperatureto reflux
  9. temperaturemaintained
  10. temperatureat reflux for 49 hours
  11. temperatureThe reaction mixture was then cooled
  12. concentrationconcentrated on a rotary evaporator at 55° C
  13. customtransferred to a separatory funnel
  14. washwashed consecutively with 100 milliliter portions each of water, 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water
  15. customThe organic layer was separated
  16. dry with materialdried over magnesium sulfate
  17. concentrationconcentrated on a rotary evaporator at 55° C.
  18. customleaving a dark liquid residue
  19. additionThe dark liquid was charged to a distillation flask
  20. distillationdistilled at a pressure of 1.8 millimeters of mercury
  21. customA main fraction (14.98 grams) was collected

Sources & evidence

ORD record
ord-5424724287c24f0ca5b9e10b44318452
Source dataset
uspto-grants-1982_09
Patent number
US04348223

Reaction notes

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