Chloroacetonitrile → 2-(2'-Nitro-4-biphenylyl)propionic acid

HRID 436616ノート

反応式

HRID 436616 の反応式
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]

参加物

4

反応物 3

HCID 7856ChloroacetonitrileHCID 21453329Methyl 2-(2'-nitro-4-biphenylyl)propionateHCID 23665649Lithium perchlorate

生成物 1

HCID 214533272-(2'-Nitro-4-biphenylyl)propionic acid

実験手順

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.

出典と根拠

ORDレコード
ord-f8188bdc57cf460499a775f9873ce79f
出典データセット
uspto-grants-1977_02
特許番号
US04009283

反応ノート

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