Diethyl Ether → 4-(But-3-en-1-yl)-1,1'-biphenyl

HRID 1390608Notes

Reaction equation

HRID 1390608 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Mg].O(CC)CC.Br[CH2:22][CH:23]=[CH2:24]>O1CCCC1>[CH2:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH2:24][CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 154634-Phenylbenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 201456254-(But-3-en-1-yl)-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 89 parts of 4-(chloromethyl)-1,1'-biphenyl and 12.5 parts of magnesium in 350 parts of 1,1'-oxybisethane, is added dropwise a solution of 60 parts of 3-bromo-1-propene in 180 parts of tetrahydrofuran. Upon completion, stirring is continued for 2.50 hours at reflux temperature. The reaction mixture is cooled and poured onto water. The layers are separated and the aqueous phase is extracted with 1,1'-oxybisethane. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is filtered and the filtrate is evaporated, yielding 60 parts of 4-(3-butenyl)-1,1'-biphenyl as a residue.

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. temperatureThe reaction mixture is cooled
  6. additionpoured onto water
  7. customThe layers are separated
  8. extractionthe aqueous phase is extracted with 1,1'-oxybisethane
  9. washThe combined organic phases are washed with water
  10. customdried
  11. filtrationfiltered
  12. customevaporated
  13. filtrationThe residue is filtered
  14. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-79955def94e548a7b83c792fbc79af88
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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