Benzene → 1-(4-Chlorophenyl)-1-cyclopropyl4-(3-phenoxyphenyl)butane

HRID 1383229Notes

Reaction equation

HRID 1383229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:25]2[CH2:27][CH2:26]2)=[CH:9][CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.C1C=CC=CC=1.[H][H]>[Pd].C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:25]2[CH2:26][CH2:27]2)[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 241BenzeneHCID 541076381-(4-Chlorophenyl)-1-cyclopropyl-4-(3-phenoxyphenyl)1,3-butadieneHCID 178418361HCID 178418361, compound

Product 1

HCID 212741601-(4-Chlorophenyl)-1-cyclopropyl4-(3-phenoxyphenyl)butaneYield 23%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.3 grams (0.006 mole) of 1-(4-chlorophenyl)-1-cyclopropyl-4-(3-phenoxyphenyl)-1,3-butadiene, 2.3 grams (0.002 mole) of 10% palladium on carbon, 0.25 gram (0.0002 mole) of tris(triphenylphosphine)rhodium (I) chloride, and 25 mL of benzene in 100 mL of ethanol was hydrogenated at 40° C. using a Parr hydrogenator. Upon completion of the uptake of the theoretical amount of hydrogen (two hours), the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was taken up in hexane and filtered. The filtrate was dried with sodium sulfate and filtered again. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to rotating disk thin layer chromatography. Elution was accomplished using 20% toluene in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.52 gram of 1-(4-chlorophenyl)-1-cyclopropyl4-(3-phenoxyphenyl)butane as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customwas hydrogenated at 40° C.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. filtrationfiltered
  5. dry with materialThe filtrate was dried with sodium sulfate
  6. filtrationfiltered again
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-562c566a79fd4d43aeb0d8f931ba0011
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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