Nitric Acid → HCID 68288276, compound

HRID 541226Notes

Reaction equation

HRID 541226 reaction equation
[CH2:1]([C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[CH:11]=[C:10]([CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19886963HCID 19886963, compound2×

Product 1

HCID 68288276HCID 68288276, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a stirred mixture of 2-ethyl-4-methylbenzoic acid (compound 48.2, 2 g, 12.18 mmol, 1.00 equiv) in sulfuric acid (30 mL) at −10° C. was added dropwise a solution of nitric acid (1.6 g, 16.50 mmol, 2.08 equiv) in sulfuric acid (10 mL). After stirring for 30 min at −10° C., 200 mL of H2O/ice was carefully added and the resulting mixture was extracted with 50 mL of ethyl acetate. The organic phase was washed with 2×50 mL of brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by re-crystallization from ethyl acetate/petroleum ether in the ratio 1:10 to yield 1.0 g (37%) of 2-ethyl-4-methyl-5-nitrobenzoic acid as a light-yellow solid.

Workup

  1. extractionthe resulting mixture was extracted with 50 mL of ethyl acetate
  2. washThe organic phase was washed with 2×50 mL of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by re-crystallization from ethyl acetate/petroleum ether in the ratio 1:10

Sources & evidence

ORD record
ord-a5671fb7d2c447a6a8a528fbaf882027
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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