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

HRID 1856511

반응식

HRID 1856511 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-86956048702143539d2b0518aac199fd
출처 데이터셋
uspto-grants-1980_08
특허 번호
US04219668

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