Chloroacetonitrile → 2-(2'-Nitro-4-biphenylyl)propionic acid
Reaction equation
ClCC#N.Cl([O-])(=O)(=O)=O.[Li+].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:31])[C:27]([O:29]C)=[O:28])=[CH:22][CH:21]=1)([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:31])[C:27]([OH:29])=[O:28])=[CH:22][CH:21]=1)([O-:13])=[O:12]Participants
4
Procedure
The 2-(2'-nitro-4-biphenylyl)propionic acid is readily prepared in the following manner: 2-nitrobiphenyl is acylated with acetyl chloride, giving 4-acetyl-2'-nitrobiphenyl. This is converted with chloroacetonitrile under alkaline conditions to the intermediate isomeric 2-methyl-2-[4-(2'-nitrophenyl)]glycidonitriles which, when treated with lithium perchlorate and then base, is isomerized to methyl 2-(2'-nitro-4-biphenylyl)propionate. Saponificiation of the latter gives the desired 2-(2'-nitro-4-biphenylyl)-propionic acid. The esters are readily converted to the acid and the acid to the esters by conventional means.
Sources & evidence
- ORD record
- ord-c643d48902fe48bf940768c68678da66
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03957861
Reaction notes
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