Nitric Acid → 4-Ethyl-3-nitrobenzoic acid

HRID 514436Notes

Reaction equation

HRID 514436 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 120864-Ethylbenzoic Acid

Product 1

HCID 81670864-Ethyl-3-nitrobenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-ethyl benzoic acid (4.53 g, 30.16 mmol) in concentrated sulfuric acid (24 mL) at 0° C. was added nitric acid (12 mL). The mixture was stirred for 1.5 h at 0° C. Poured into ice water, filtered and dried the solid to give 5.79 g of the title compound (98%). 1H NMR (400 MHz, DMSO-d6): δ 1.23 (3H, t, J=7.2 Hz), 2.88 (2H, q, J=7.2 Hz), 7.67 (1H, d, J=8.0 Hz), 8.15 (1H, dd, J=1.6, 8.0 Hz), 8.36 (1H, d, J=1.6 Hz).

Workup

  1. filtrationfiltered
  2. customdried the solid

Sources & evidence

ORD record
ord-2287eb4cc38a498ab5d23e8db6928ee5
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

Loading…