Methanol → Methyl 4-Iodo-3-methylbenzoate

HRID 1137

Reaction equation

HRID 1137 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15173224-Iodo-3-methylbenzoic acid

Product 1

HCID 231757Methyl 4-Iodo-3-methylbenzoate

Procedure

24.4 g (0.093 mol) of 3-methyl-4-iodobenzoic acid and 250 ml of methanol were introduced into a round-bottomed flask and 2.5 ml of concentrated sulfuric acid were added dropwise. The mixture was heated at reflux for twelve hours, the reaction medium evaporated, taken up in ethyl acetate and water, the organic phase decanted off, dried over magnesium sulfate and evaporated. The residue was triturated in methanol and filtered; 21.9 g (85%) of the expected methyl ester of melting point 58°-59° C. were recovered.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for twelve hours
  3. customthe reaction medium evaporated
  4. customwater, the organic phase decanted off
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated in methanol
  8. filtrationfiltered
  9. custom21.9 g (85%) of the expected methyl ester of melting point 58°-59° C. were recovered

Sources & evidence

ORD record
ord-9664b54f4f6141978a503b896b8ef7fd
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Linked notes

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