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

HRID 1856511

Reaction equation

HRID 1856511 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-86956048702143539d2b0518aac199fd
Source dataset
uspto-grants-1980_08
Patent number
US04219668

Linked notes

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