Methyl iodide → Methyl 3-methyl-4-nitrobenzoate

HRID 1577142Notes

Reaction equation

HRID 1577142 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].IC.[C:16](=O)(O)[O-].[Na+]>CC(N(C)C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:16])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 183703-Methyl-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 260927Methyl 3-methyl-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-Methyl-4-nitrobenzoic acid (67 g, 0.37 mole) is added to a mixture of dimethylacetamide (300 ml), iodomethane (85 g, 1.0 mole) and anhydrous sodium bicarbonate (84 g, 1.0 mole). The mixture is stirred and heated at reflux for two hours. The mixture is cooled, and filtered and the solids are washed with methanol before being discarded. The filtrate and washings are evaporated to a residue which crystallizes. Recrystallization from diethyl ether gives pure methyl 3-methyl-4-nitrobenzoate, 65.1 g, m.p. 73°-75.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washthe solids are washed with methanol
  6. customThe filtrate and washings are evaporated to a residue which
  7. customcrystallizes
  8. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-805fb05f1f154c748b4746698cc4d254
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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