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

HRID 968776Notes

Reaction equation

HRID 968776 reaction equation
[CH3:1][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].S(Cl)(Cl)=O.[CH3:21]O>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:8][CH3:21])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 854773,5-Dinitro-p-toluic acid

Product 1

HCID 4366501Methyl 4-methyl-3,5-dinitrobenzoateYield 90%

Procedure

To a mixture of 4-methyl-3,5-dinitro-benzoic acid (3) (35.1 g, 155 mmol) in anhydrous methanol (250 mL) is slowly added thionyl chloride (4 mL, 54 mmol). The resulting solution is heated to reflux for 16 hours. The solution is cooled to room temperature and then further cooled in an ice-water bath. The solid that forms is filtered and dried to give 4-methyl-3,5-dinitro-benzoic acid, methyl ester (32) (33.5 g, 139.5 mmol, 90% yield), as a white crystalline solid.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for 16 hours
  3. temperaturefurther cooled in an ice-water bath
  4. filtrationThe solid that forms is filtered
  5. customdried

Sources & evidence

ORD record
ord-425c8c17b6f943ba855a618ec5bd0a3f
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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