Benzoate → 2-Nitrobenzoic acid
Reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O.C(OC(=O)C)(=O)C>>[N+:10]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:1]([OH:9])=[O:8])([O-:12])=[O:11]Participants
5
Procedure
Substantially equimolar amounts of 2,5-dichlorobenzoxazole and the potassium salt of 2-hydroxy benzoic acid are reacted, in an inert organic solvent, e.g., dimethylsulfoxide, in the presence of acetic acid giving 5-(5-chloro-2-benzoxazolyloxy) benzoic acid. The benzoate is then nitrated by, for example, reaction with a mixture of nitric acid, sulfuric acid and acetic anhydride to give the corresponding 2-nitrobenzoic acid prepared as previously described. The 2-nitrobenzoic acid is then reacted with ethyl 2-chloropropionate, as previously described, giving the desired 1-(ethoxycarbonyl)ethyl 5-(5-chloro-2-benzoxazolyloxy)-2-nitrobenzoate.
Sources & evidence
- ORD record
- ord-48e414eaa8714cc8a62979394fe9369f
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04468244
Reaction notes
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