Nitric Acid → 2-Iodo-5-nitrobenzoic acid

HRID 381289

Reaction equation

HRID 381289 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[I:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 69412-Iodobenzoic acid

Product 1

HCID 38487452-Iodo-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2-Iodobenzoic acid (100 g) was dissolved in 400 mL of concentrated sulphuric acid and placed in a 2 liter 3 necked flask. The flask was fitted with reflux condenser, a thermometer and an addition funnel. Fuming nitric acid (400 ml) was added drop by drop. The addition was adjusted in such a way that the temperature was allowed to raise to 80° C. over a period of 2 hours. During the addition, the reaction mixture was stirred vigorously and maintained the temperature at 80° C. for an additional 2 hours. After the completion of the reaction, the reaction mixture was poured slowly into crushed ice (3 Kg). The contents were allowed to settle and were filtered. The yellow precipitate was collected and dried at 30° C. The yield was 90 grams.

Workup

  1. customThe flask was fitted
  2. temperaturewith reflux condenser
  3. additionThe addition
  4. additionDuring the addition
  5. temperaturemaintained the temperature at 80° C. for an additional 2 hours
  6. customAfter the completion of the reaction
  7. additionthe reaction mixture was poured slowly
  8. filtrationwere filtered
  9. customThe yellow precipitate was collected
  10. customdried at 30° C

Sources & evidence

ORD record
ord-aa26efb129544d54a21061960d2ba5b5
Source dataset
uspto-grants-2001_10
Patent number
US06306871B1

Linked notes

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