Sulfuric Acid → 2-Isopropyl-4-nitro-benzoic acid

HRID 1910759Notes

Reaction equation

HRID 1910759 reaction equation
[CH:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8]C=1C#N)([CH3:3])[CH3:2].S(=O)(=O)(O)[OH:16].[O:20]1[CH2:25][CH2:24]OCC1>>[CH:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:24]=1[C:25]([OH:20])=[O:16])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 671066302-Isopropyl-4-nitro-benzonitrile

Product 1

HCID 671058552-Isopropyl-4-nitro-benzoic acidYield 52%

Procedure

2-Isopropyl-4-nitro-benzonitrile (0.4 g, 2.10 mmol) was dissolved in dioxane (10 mL) and 80% sulfuric acid (10 mL) was added. The mixture was heated at reflux for 2 days then dioxane was evaporated under reduced pressure. The residue was basified with dilute sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was then acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was separated, washed with water and brine, dried over sodium sulfate and concentrated to yield 2-isopropyl-4-nitro-benzoic acid (0.23 g, 52%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 days
  3. customdioxane was evaporated under reduced pressure
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was separated
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8b26a7b5192d49b7ac89f0c8721010b0
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

Loading…