Nitric Acid → 2-(2-Methyl-5-nitrophenyl)acetic acid

HRID 889448Notes

Reaction equation

HRID 889448 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18]>C(Cl)Cl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([N+:17]([O-:19])=[O:18])=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 69519o-Tolylacetic acid

Product 1

HCID 224753382-(2-Methyl-5-nitrophenyl)acetic acidYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 2-o-tolylacetic acid (3.54 g, 23.6 mmol) in DCM (12 mL) was added to a pre-cooled mixture of concentrated sulfuric acid (10 mL, 188 mmol) and 90% nitric acid (1 mL, 22.4 mmol) at −20° C. The reaction mixture was stirred at −20° C. for 30 minutes, then slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into ice-water. The white solid was collected by filtration, rinsed with water, and concentrated. The solid was triturated with ether and filtered to obtain Intermediate 80A (2.4 g, 42%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.62 (1H, br. s.), 8.13 (1H, d, J=2.51 Hz), 8.04 (1H, dd, J=8.28, 2.51 Hz), 7.47 (1H, d, J=8.53 Hz), 3.80 (2H, s), 2.34 (3H, s).

Workup

  1. temperatureslowly warmed to room temperature
  2. stirringstirred overnight
  3. filtrationThe white solid was collected by filtration
  4. washrinsed with water
  5. concentrationconcentrated
  6. customThe solid was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4295bd4fb55c434eb69dbed4b824da2a
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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