Methanol → Methyl 4-nitrobenzoate

HRID 1733677

Reaction equation

HRID 1733677 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:13](Cl)(Cl)Cl.CO>C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:13])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 61084-Nitrobenzoic AcidHCID 6212Chloroform

Product 1

HCID 12083Methyl 4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

p-Nitrobenzoic acid (1.67 g) is suspended into chloroform (20 ml) and thereto are added triethylamine (1.40 ml) under ice-cooling and further 1-(p-chlorobenzenesulfonyoxy)-6-chloro-1,2,3-benzotriazole (3.44 g). When the mixture is stirred at room temperature for 15 minutes, yellow precipitates are produced and the mixture is further stirred for 5 hours. To the mixture are added methanol (0.6 ml) and triethylamine (1.4 ml), whereby the precipitates are dissolved. After stirring for 1 hour, chloroform is distilled off and the residue extracted with ethyl acetate. The extract is washed with water, an aqueous sodium hydrogen carbonate, 1 N hydrochloric acid and water in order and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off. The resulting crystals aare recrystallized from isopropyl alcohol to give yellow crystals of methyl p-nitrobenzoate (1.4 g), melting point: 93°-94° C.

Workup

  1. temperaturecooling
  2. customyellow precipitates
  3. customare produced
  4. stirringthe mixture is further stirred for 5 hours
  5. dissolutionare dissolved
  6. stirringAfter stirring for 1 hour
  7. distillationchloroform is distilled off
  8. extractionthe residue extracted with ethyl acetate
  9. washThe extract is washed with water
  10. dry with materialan aqueous sodium hydrogen carbonate, 1 N hydrochloric acid and water in order and dried over anhydrous magnesium sulfate
  11. customAfter drying
  12. distillationthe solvent is distilled off
  13. customThe resulting crystals aare recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-38c941003c3a46d3a356f2807d976bd2
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Linked notes

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