Methanol → Methyl 4-Iodo-3-methylbenzoate

HRID 861800Notes

Reaction equation

HRID 861800 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. Heating was carried out at reflux for twelve hours, the reaction mixture was evaporated and the residue taken up in ethyl acetate and water. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue was triturated in methanol and filtered. 21.9 g (85%) of the expected methyl ester, with a melting point of 58°-59° C., were recovered.

Workup

  1. temperatureHeating
  2. temperatureat reflux for twelve hours
  3. customthe reaction mixture was evaporated
  4. customThe organic phase was separated
  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, with a melting point of 58°-59° C., were recovered

Sources & evidence

ORD record
ord-691b2990c859480f9ecc656fe9c3e3c5
Source dataset
uspto-grants-1998_02
Patent number
US05716624

Reaction notes

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