Succinic anhydride → 4-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

HRID 1856511

反応式

HRID 1856511 の反応式
[OH:1][CH:2]([C:8]1(O)[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:21][O:22]C1C=CC(C2C=CC=CC=2)=CC=1.C1(=O)OC(=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:21][O:22][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:2](=[O:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 7922Succinic anhydrideHCID 119434-MethoxybiphenylHCID 6451240Aluminum(III) ChlorideHCID 86737169gamma,4-Dihydroxy-4-biphenylbutyric acid

生成物 1

HCID 230052384-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

実験手順

γ,4-dihydroxy-4-biphenylbutyric acid may be prepared by treating p-methoxybiphenyl with succinic anhydride in nitrobenzene. The mixture is treated with aluminum chloride at reduced temperature. The solid is dissolved in aqueous base with heat, chilled to reprecipitate and acidified giving 4'-methoxy-γ-oxo-4-biphenylbutyric acid. This intermediate is refluxed with hydrogen bromide for several hours, diluted with water and cooled. The precipitate is 4'-hydroxy-γ-oxo-biphenylbutyric acid. This intermediate is treated with sodium borohydride in an alkaline medium and then acidified giving the desired product.

後処理

  1. dissolutionThe solid is dissolved in aqueous base
  2. temperaturewith heat
  3. temperaturechilled

出典と根拠

ORDレコード
ord-86956048702143539d2b0518aac199fd
出典データセット
uspto-grants-1980_08
特許番号
US04219668

関連ノート

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