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. 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
- temperatureHeating
- temperatureat reflux for twelve hours
- customthe reaction mixture was evaporated
- customThe organic phase was separated
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was triturated in methanol
- filtrationfiltered
- custom21.9 g (85%) of the expected methyl ester, with a melting point of 58°-59° C., were recovered
Sources & evidence
- ORD record
- ord-28e714b4d999404bbb4c92a95d3104a7
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06368608B1
Linked notes
Loading…