Methanol → Methyl 3-chloro-2-methylbenzoate
Reaction equation
[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-chloro-2-methylbenzoic acid (1.00 g, 5.86 mmol) in methanol (25 mL) was added 3 drops of sulfuric acid. The mixture was stirred at reflux for 18 h. After concentrating the residue was dissolved in ether, washed with 10% sodium hydroxide solution, brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 0.95 g (88%) of the title compound as a white solid: 1H NMR (250 MHz, CDCl3) d 7.62 (d, 1H), 7.41 (d, 1H), 7.05 (t, 1H), 3.82 (s, 3H), 2.55 (s, 3H).
Workup
- temperatureat reflux for 18 h
- concentrationAfter concentrating the residue
- dissolutionwas dissolved in ether
- washwashed with 10% sodium hydroxide solution, brine
- dry with materialdried (Na2SO4)
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-0ad5d0a6cf7e4e9ab170f07fd43ee5dc
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958968
Reaction notes
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