Nitric Acid → (4-Methyl-3-nitrophenyl)acetic acid

HRID 1180208Notes

Reaction equation

HRID 1180208 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 248474p-Tolylacetic acid

Product 1

HCID 18186407(4-Methyl-3-nitrophenyl)acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylphenylacetic acid (1.50 g, 10.0 mmol) in dried dichloromethane was added nitric acid (fuming, 1.5 mL) dropwise. The mixture was stirred at room temperature for 2 hours, then quenched with water and extracted with ethyl acetate. The extracts were washed with water twice and brine, dried over magnesium sulfate, filtered, and concentrated to provide the title compound (1.66 g, 85% yield): 1H NMR (CDCl3) 7.91 (d, 1H), 7.42 (dd, 1H), 7.31 (d, 1H), 3.71 (s, 2H), 2.58 (s, 3H); ES-MS m/z 196 [M+H]+.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water twice
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a76edc2bb1d24be5a61adf2ab07453d0
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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