Methanol → HCID 54552579, compound

HRID 839060Notes

Reaction equation

HRID 839060 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:20]([O-:22])=[O:21])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:28]O>>[CH3:28][O:8][C:7](=[O:9])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12408765HCID 12408765, compound

Product 1

HCID 54552579HCID 54552579, compound

Procedure

30 g of 3,5-dinitro-4-phenoxy-benzoic acid in 200 ml of methanol are combined with 3 ml of concentrated sulphuric acid and the whole is boiled for 3 hours under reflux. After evaporation of the solvent, the residue is dissolved in ethyl acetate, and traces of unreacted acid are destroyed with dilute sodium bicarbonate solution. After drying of the ethyl acetate solution, the solvent is eliminated by evaporation, the residue is recrystallised from ethyl acetate/methanol. The desired ester melting at 171°-173° C is obtained with a very good yield.

Workup

  1. temperatureunder reflux
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. customtraces of unreacted acid are destroyed with dilute sodium bicarbonate solution
  5. dry with materialAfter drying of the ethyl acetate solution
  6. customthe solvent is eliminated by evaporation
  7. customthe residue is recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-05ea78acf5a64982a05aedad634ee8d5
Source dataset
uspto-grants-1978_06
Patent number
US04093735

Reaction notes

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