4-(3,4-Dichlorophenyl)-4-phenylbut-3-enoic acid → 4-(3,4-Dichlorophenyl)-4-phenylbutanoic acid

HRID 637385Notes

Reaction equation

HRID 637385 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 542973774-(3,4-Dichlorophenyl)-4-phenylbut-3-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 99047234-(3,4-Dichlorophenyl)-4-phenylbutanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3,4-dichlorophenyl)-4-phenylbut-3-enoic acid (223 g., 0.73 mole) in ethyl acetate (2 l.) was hydrogenated over 8 grams of 5% Pd/C catalyst at atmospheric pressure and room temperature until hydrogen uptake ceased (about 24 hours). The catalyst was separated by filtration and the filtrate evaporated under vacuum to a light brown oil containing traces of solvent (ca. 100% yield). An analytical sample of the named compound was crystallized from hexane (m.p. 118°-120° C., elemental analysis calculated: 62.17% C; 4.57% H; 22.94% Cl; found: 62.08% C; 4.56% H; 23.16% Cl).

Workup

  1. custom(about 24 hours)
  2. customThe catalyst was separated by filtration
  3. customthe filtrate evaporated under vacuum to a light brown oil

Sources & evidence

ORD record
ord-b6c87fb0012a4aee83c69d5ef9f26682
Source dataset
uspto-grants-1985_12
Patent number
US04556676

Reaction notes

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