Methanol → Benzoic acid, 2,5-diiodo-, methyl ester

HRID 1802596Notes

Reaction equation

HRID 1802596 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:16]O>>[I:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 26549Benzoic acid, 2,5-diiodo-

Product 1

HCID 10883593Benzoic acid, 2,5-diiodo-, methyl ester

Procedure

To a solution of 2,5-diiodobenzoic acid (1.00 g, 2.67 mmol) in anhydrous MeOH (15 mL) cooled in an ice-bath, SOCl2 (0.50 mL, 6.85 mmol) was cautiously added (exothermal reaction). After the addition, the solution was heated at reflux overnight. It was then concentrated in vacuo to give methyl 2,5-diiodobenzoate (1.04 g).

Workup

  1. custom(exothermal reaction)
  2. additionAfter the addition
  3. temperaturethe solution was heated
  4. temperatureat reflux overnight
  5. concentrationIt was then concentrated in vacuo

Sources & evidence

ORD record
ord-84f4aa5f865d40ccb7c410f66a291a3f
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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