Methanol → Methyl 4-chloro-3,5-dinitrobenzoate

HRID 372251Notes

Reaction equation

HRID 372251 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 83774-Chloro-3,5-dinitrobenzoic acid

Product 1

HCID 96161Methyl 4-chloro-3,5-dinitrobenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Chloro-3,5-dinitrobenzoic acid (25.0 gm.) is dissolved in a cooled solution of methanol (125 ml.) and concentrated sulfuric acid (3.0 ml.). The reaction mixture is allowed to warm to room temperature and then heated to reflux for 18 hours. The product precipitated as light yellow needles on cooling, which are collected by filtration and washed with 15 ml. of methanol (24.0 gm., m.p. 102°-104.5°). Recrystallization from methanol gives light yellow needles (23.6 g., m.p. 104°-105.5°, 89% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe product precipitated as light yellow needles
  4. temperatureon cooling
  5. filtrationwhich are collected by filtration
  6. washwashed with 15 ml
  7. customRecrystallization from methanol
  8. customgives light yellow needles (23.6 g., m.p. 104°-105.5°, 89% yield)

Sources & evidence

ORD record
ord-e439786851814de4a5af3ca742862529
Source dataset
uspto-grants-1978_05
Patent number
US04089973

Reaction notes

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