Methanol → Methyl 4-Iodo-3-methylbenzoate

HRID 1275622Notes

Reaction equation

HRID 1275622 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 12 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, filtered and 21.9 g (85%) of the expected methyl ester of melting point 58-9° C. were recovered.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 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 58-9° C. were recovered

Sources & evidence

ORD record
ord-ea318a8667bf49ed9f0d3949a015777e
Source dataset
uspto-grants-2000_12
Patent number
US06162815

Reaction notes

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