Methanol → Methyl 2-iodo-5-nitrobenzoate

HRID 1837288Notes

Reaction equation

HRID 1837288 reaction equation
[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].S(=O)(=O)(O)O.[CH3:19]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]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 38487452-Iodo-5-nitrobenzoic acid

Product 1

HCID 11415548Methyl 2-iodo-5-nitrobenzoate

Procedure

In a 5 liter 3 necked flask, 2-iodo-5-nitro-benzoic acid (100 grams) was dissolved in methanol (3000 ml). The flask was fitted with a reflux condenser and 50 ml of concentrated sulfuric acid was added carefully with cooling. After the completion of the addition, the contents were refluxed for 3 days until completion of the reaction. The reaction was followed by TLC. After the completion of the reaction, the reaction mixture was concentrated to 1000 ml and allowed to cool. The product crystalized as a light yellow colored powder. The solid material was filtered and washed with water and methanol and air-dried. The yield was 90 grams.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperaturewith cooling
  3. additionAfter the completion of the addition
  4. temperaturethe contents were refluxed for 3 days until completion of the reaction
  5. customAfter the completion of the reaction
  6. concentrationthe reaction mixture was concentrated to 1000 ml
  7. temperatureto cool
  8. customThe product crystalized as a light yellow colored powder
  9. filtrationThe solid material was filtered
  10. washwashed with water and methanol
  11. customair-dried

Sources & evidence

ORD record
ord-c6abd32d55bf44b0b134c353bf83b674
Source dataset
uspto-grants-2004_08
Patent number
US06780995B2

Reaction notes

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