Nitric Acid → m-Nitrobenzenephosphonous acid
Reaction equation
C1(P(Cl)Cl)C=CC=CC=1.[C:10]1([P:16]([OH:18])[OH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:19]([O-])([OH:21])=[O:20]>>[N+:19]([C:12]1[CH:11]=[C:10]([P:16]([OH:18])[OH:17])[CH:15]=[CH:14][CH:13]=1)([O-:21])=[O:20]Participants
Procedure
According to my invention phenylphosphorus dichloride is converted to benzenephosphonous acid (B), which is nitrated (I) with nitric acid at a temperature around 0° C. to form m-nitrobenzenephosphonous acid (E) which, to my knowledge, is a compound not previously described in the literature. Compound E is conveniently oxidized by heating (II) the reaction mixture in the presence of additional nitric acid to form m-nitrobenzenephosphonic acid (C), and then compound (D) by subsequent reduction. My contribution, then, includes the nitration of benzenephosphonous acid (B), which is considerably less costly than benzenephosphonic acid (A), to form the novel compound m-nitrobenzenephosphonous acid (E), followed by oxidation to form m-nitrobenzene phosphonic acid (C) which is converted by conventional reduction to form the desired m-aminobenzenephosphonic acid (D).
Workup
- customat a temperature around 0° C.
Sources & evidence
- ORD record
- ord-9c65efd26ece43ae9c931f15cece7eeb
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04028403
Reaction notes
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