Methanol → Methyl 3-methoxy-4-nitrobenzoate

HRID 1458697Notes

Reaction equation

HRID 1458697 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([OH:12])=[O:11].[CH3:19]O>>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([O:12][CH3:19])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoateYield 97%

Procedure

Thionyl chloride (3.7 g) was added dropwise under ice cooling to a solution of 4.7 g (24 mmol) of 3-methoxy-4-nitrobenzoic acid in 250 ml of methanol. The thus-obtained mixture was stirred at room temperature for 2 hours and then stirred under heating and reflux for 3 hours. After the solvent was distilled out under reduced pressure, the residue was neutralized with aqueous ammonia and then extracted with methylene chloride. The extract was dried over sodium sulfate and then dried up under reduced pressure, whereby 4.9 g of white powder were obtained (yield: 97%).

Workup

  1. stirringstirred
  2. temperatureunder heating
  3. temperaturereflux for 3 hours
  4. distillationAfter the solvent was distilled out under reduced pressure
  5. extractionextracted with methylene chloride
  6. dry with materialThe extract was dried over sodium sulfate
  7. customdried up under reduced pressure

Sources & evidence

ORD record
ord-736d7c5d3594459184235079dd38c206
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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