Methanol → Methyl 4-Iodo-3-methylbenzoate
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
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
- temperatureThe mixture was heated
- temperatureat reflux for twelve hours
- customthe reaction medium evaporated
- customwater, the organic phase decanted off
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was triturated in methanol
- filtrationfiltered
- 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
Reaction notes
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