Nitric Acid → 4-Chloro-2-methyl-3-nitrobenzoic acid

HRID 1161291Notes

Reaction equation

HRID 1161291 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 107039094-Chloro-2-methyl-3-nitrobenzoic acid

Conditions

Temperature
70 °C

Procedure

A round bottom flask was charged with 4-chloro-2-methylbenzoic acid (200 mg, 0.001 mol) and sulfuric acid (1 mL, 0.02 mol) and fuming nitric acid (0.05 mL, 0.001 mol) was added at −20° C. and the reaction stirred for 1 hour at 70° C. and poured into ice cold water wherein the mixture of 2- and 4-nitro compounds precipitated out. The precipitate was filtered and dissolved in ethylacetate (30 mL) and washed with saturated aqueous sodium bicarbonate solution, brine and dried over sodium sulfate. The solvent was reduced ¼ volume, and the undesired isomer precipitated out. The precipitate was filtered and the filtrate was dried to obtain a 1:1 mixture of isomers as a white solid. MS m/z=214.5 (M−H).

Workup

  1. additionwas added at −20° C.
  2. additionpoured into ice cold water wherein
  3. customprecipitated out
  4. filtrationThe precipitate was filtered
  5. dissolutiondissolved in ethylacetate (30 mL)
  6. washwashed with saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. customthe undesired isomer precipitated out
  9. filtrationThe precipitate was filtered
  10. customthe filtrate was dried
  11. customto obtain
  12. additiona 1:1 mixture of isomers as a white solid

Sources & evidence

ORD record
ord-76fa540df6ae4585b02939d2a41f3fec
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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