Sulfuric Acid → Benzoic acid, 2-iodosyl-4-nitro-

HRID 968277Notes

Reaction equation

HRID 968277 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4]C=1C.C([O:15][C:16](=[O:18])[CH3:17])(=O)C.S(=O)(=O)(O)[OH:20]>[O-2].[O-2].[O-2].[Cr+6].C(O)(=O)C>[I:1]([C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:17]=1[C:16]([OH:15])=[O:18])=[O:20]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 821882-Iodo-4-nitrotoluene

Product 1

HCID 3714830Benzoic acid, 2-iodosyl-4-nitro-

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-iodo-4-nitrotoluene (50 g, 0.19 mol) in a mixture of glacial acetic acid (380 ml), acetic anhydride (190 ml) and concentrated sulfuric acid (112 ml) was cooled in an ice bath. Chromium trioxide (97 g, 0.57 mol) was added portionwise over 30 minutes, during which time the internal temperature rose to ca. 90° C. The resultant thick suspension was cooled in an ice bath for 30 min, then poured over ice (2 kg). When the ice had melted, the precipitate was collected by filtration, washed with methanol (800 ml) and ether (200 ml), and dried in vacuo to afford 2-iodosyl-4-nitro-benzoic acid I-1a (54.9 a, 94%).

Workup

  1. temperaturewas cooled in an ice bath
  2. customrose to ca. 90° C
  3. temperatureThe resultant thick suspension was cooled in an ice bath for 30 min
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with methanol (800 ml) and ether (200 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-76a1c87a39a647bea16b3b39d661fe60
Source dataset
uspto-grants-2005_10
Patent number
US06958347B2

Reaction notes

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