Methanol → Methyl 3-iodobenzoate

HRID 1197784Notes

Reaction equation

HRID 1197784 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:16]O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120603-Iodobenzoic acid

Product 1

HCID 69258Methyl 3-iodobenzoate

Procedure

To a stirred solution of 25 g (100.8 mmol) of 3-iodobenzoic acid in 250 mL of methanol under argon was added 1.2 mL (23.2 mmol) of concentrated H2SO4 and the mixture was heated to reflux for 24 h. The solution was concentrated to 150 mL, gravity filtered to remove any insoluble material, scratched with a glass rod, and allowed to cool slowly. After cooling to RT the flask was allowed to stand in the refrigerator for a few days. The solid was collected and washed with ice cold methanol and dried under high vacuum at RT for 2 days to provide 25.7 g (97%) of a light violet colored solid. mp 40°-41° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationThe solution was concentrated to 150 mL, gravity
  4. filtrationfiltered
  5. customto remove any insoluble material
  6. temperatureto cool slowly
  7. waitto stand in the refrigerator for a few days
  8. customThe solid was collected
  9. washwashed with ice cold methanol
  10. customdried under high vacuum at RT for 2 days
  11. customto provide 25.7 g (97%) of a light

Sources & evidence

ORD record
ord-e760b8a7f7d84079b3753cddc97062a7
Source dataset
uspto-grants-1994_01
Patent number
US05278153

Reaction notes

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