Methanol → Methyl 2-chloro-3-nitrobenzoate
Reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:19]O>C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-chloro-3-nitrobenzoic acid (543.6 g, 2.7 mol) was suspended in methanol (3425.0 ml), and concentrated sulfuric acid (108.5 ml) was added thereto. The mixture was heated to reflux for 6 hours. The mixture was cooled to room temperature, and then the solvent was concentrated under reduced pressure. The concentration residue was added into a saturated aqueous solution of sodium bicarbonate. A solid that precipitated was filtered, and washed with water. The solid thus obtained was dissolved in ethyl acetate, washed with saturated saline, and then dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, the filtrate was concentrated and dried to solid under reduced pressure, and the resultant solid was washed with n-hexane. As a result, 542.6 g (yield: 93%) of the indicated compound was obtained
Workup
- temperatureThe mixture was heated
- temperatureto reflux for 6 hours
- concentrationthe solvent was concentrated under reduced pressure
- additionThe concentration residue was added into a saturated aqueous solution of sodium bicarbonate
- customA solid that precipitated
- filtrationwas filtered
- washwashed with water
- customThe solid thus obtained
- washwashed with saturated saline
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe sodium sulfate was filtered away
- concentrationthe filtrate was concentrated
- customdried to solid under reduced pressure
- washthe resultant solid was washed with n-hexane
Sources & evidence
- ORD record
- ord-558fcfef96ee4fd1b79b10feb92e942a
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853440B2
Reaction notes
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