Methanol → Methyl 4-iodobenzoate

HRID 1274253Notes

Reaction equation

HRID 1274253 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11]O>S(=O)(=O)(O)O>[CH3:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 120854-Iodobenzoic acid

Product 1

HCID 69273Methyl 4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-iodobenzoic acid (5.0 g in a mixture of 50 mL methanol and 2.2 mL of conc. sulfuric acid) was heated to reflux on an oil bath. After 15 hours, the mixture was concentrated to half-volume in vacuo then poured into saturated sodium bicarbonate. This mixture was extracted with diethyl ether and the organic portion washed with brine and dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 95:5) gave the title compound (5.12 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux on an oil bath
  3. concentrationthe mixture was concentrated to half-volume in vacuo
  4. additionthen poured into saturated sodium bicarbonate
  5. extractionThis mixture was extracted with diethyl ether
  6. washthe organic portion washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customPurification of the
  9. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-4fb15ec98ea447f0ab99e71e858b74d9
Source dataset
uspto-grants-2000_12
Patent number
US06156772

Reaction notes

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