Nitric Acid → 5-Fluoro-2-methyl-3-nitrobenzoic acid

HRID 1443136Notes

Reaction equation

HRID 1443136 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[N+:17]([O-])([OH:19])=[O:18]>>[CH3:16][C:10]1[C:9]([N+:17]([O-:19])=[O:18])=[CH:8][C:7]([F:6])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 1821145-Fluoro-2-methylbenzoic acid

Product 1

HCID 179850235-Fluoro-2-methyl-3-nitrobenzoic acid

Procedure

116 ml of sulfuric acid is introduced and mixed in portions at −15° C. with 14.70 g (95.37 mmol) of 5-fluoro-2-methylbenzoic acid. A mixture of nitrating acid (4.79 ml of fuming nitric acid and 21.8 ml of concentrated sulfuric acid) is added in drops to this mixture, specifically at −15 to −10° C. during a period of 90 minutes. After three more hours of stirring, the reaction mixture is poured into ice water and stirred vigorously for about one-half hour. The precipitated crystallizate is suctioned off, washed neutral with water and dried. The yield is 8.56 g (45.1%) of a mixture of various regioisomers and by-products. This mixture is thus incorporated into the next stage (esterification) and purified in this stage.

Workup

  1. additionis added in drops to this mixture, specifically at −15 to −10° C. during a period of 90 minutes
  2. stirringstirred vigorously for about one-half hour
  3. washwashed neutral with water
  4. customdried
  5. custompurified in this stage

Sources & evidence

ORD record
ord-5da26be46ce043308965241c16271360
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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