Benzene → Methyl 2-methyl-5-nitrobenzyl ether

HRID 1075327Notes

Reaction equation

HRID 1075327 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4]Cl.[CH3:13][O-:14].[Na+].CCCCCC.C1C=CC=CC=1>CO>[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][O:14][CH3:13]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8058HexaneHCID 1879522-(Chloromethyl)-1-methyl-4-nitrobenzeneHCID 10942334Sodium Methoxide2×

Product 1

HCID 12767666Methyl 2-methyl-5-nitrobenzyl etherYield 158.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-5-nitrobenzyl chloride (10.2 g) is dissolved in methanol (180 ml). Sodium methoxide (5.4 g) is added and the mixture is refluxed. The reaction is monitored by thin layer chromatography (75:25, hexane:benzene). Additional quantities of sodium methoxide are added and heating continues until the reaction is complete. The reaction mixture is then cooled and filtered. The filtrate is concentrated under vacuum. The residue is dissolved in methylene chloride, washed with water, and the organic layer is then dried over magnesium sulfate. Removal of the drying agent by filtration and concentration of the filtrate under vacuum leaves 15.8 g of solid material which when recrystallized from hexane (150 ml) yields 11.5 g of product as a white solid having a melting point from 45° to 52° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureheating
  3. temperatureThe reaction mixture is then cooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under vacuum
  6. dissolutionThe residue is dissolved in methylene chloride
  7. washwashed with water
  8. dry with materialthe organic layer is then dried over magnesium sulfate
  9. customRemoval of the drying agent
  10. filtrationby filtration and concentration of the filtrate under vacuum

Sources & evidence

ORD record
ord-02d5e845196b4fa98572c548a5f9169f
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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