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

HRID 1382130Notes

Reaction equation

HRID 1382130 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>>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([Cl:1])=[C:10]([N+:11]([O-:13])=[O:12])[CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 83774-Chloro-3,5-dinitrobenzoic acid

Product 1

HCID 96161Methyl 4-chloro-3,5-dinitrobenzoateYield 95%

Procedure

Into a 250 ml round-bottomed flask equipped with a stirrer, thermometer and reflux condenser 74 g (0.3 mole) of 4-chloro-3,5-dinitro-benzoic acid, 128 g (4.0 mole) methanol and 14 g of concentrated sulfuric acid are introduced. The reaction mixture is refluxed under stirring for 8 hours, whereupon it is cooled to room temperature. The precipitated desired compound is filtered off, washed with 20 ml of cold methanol and dried. Thus 74.2 g of the desired compound are obtained, yield 95%, purity 99%.

Workup

  1. customInto a 250 ml round-bottomed flask equipped with a stirrer
  2. additionare introduced
  3. temperatureThe reaction mixture is refluxed
  4. customThe precipitated desired compound
  5. filtrationis filtered off
  6. washwashed with 20 ml of cold methanol
  7. customdried

Sources & evidence

ORD record
ord-e5b858cf518d488dafeebcd0408bd863
Source dataset
uspto-grants-1989_02
Patent number
US04806151

Reaction notes

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