Iodoethane → 4-Ethoxy-1,1'-biphenyl

HRID 2183429Notes

Reaction equation

HRID 2183429 reaction equation
I[CH2:2][CH3:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 71034-HydroxybiphenylHCID 11430Potassium Carbonate

Product 1

HCID 2225174-Ethoxy-1,1'-biphenylYield 166%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Iodoethane (68.7 g, 35,57 mL, 440.6 mmol) was added to a suspension of 50 g (170.2 mmol) of 4-hydroxy-1,1′-biphenyl and 40.6 g (293.75 mmol) K2CO3 in 600 mL acetone. The resulting reaction mixture was stirred under reflux for 16 hours. After cooling to room temperature the acetone was removed under reduced pressure, the residue was dissolved in ethyl acetate and extracted with water. The aqueous layers where extracted 3 times with ethyl acetate, the combined organic phases dried (Na2SO4) and evaporated to yield 56 g of the desired compound as a colorless solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 16 hours
  3. customwas removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. extractionextracted with water
  6. extractionThe aqueous layers where extracted 3 times with ethyl acetate
  7. dry with materialthe combined organic phases dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-46a497f317e24bad834bc37d5bbb63a2
Source dataset
uspto-grants-2005_05
Patent number
US06900194B1

Reaction notes

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