Acetone → 4-[(Prop-2-en-1-yl)oxy]-1,1'-biphenyl

HRID 459175Notes

Reaction equation

HRID 459175 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH3:20][C:21]([CH3:23])=O>>[CH2:23]([O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH:21]=[CH2:20]

Participants

4

Reactant 3

HCID 180AcetoneHCID 71034-HydroxybiphenylHCID 11430Potassium Carbonate

Product 1

HCID 2579864-[(Prop-2-en-1-yl)oxy]-1,1'-biphenyl

Conditions

Temperature
55 °C

Procedure

To a solution of 4-phenylphenol (1 eq) in acetone, K2CO3 (2 eq) and alkyl bromide (1.2 eq) were added and the mixture reaction was stirred at 55° C. overnight. Quenched with water and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated to give 4-allyloxybiphenyl. This crude product was dissolved in Me2NPh and heated to reflux for 6 hours and then stirred at room temperature over 3 days. Refluxed again for 8 hours and then poured into and ice-cold HCl 1M solution, extracted with ethyl acetate and washed with water. Dried and concentrated to give a crude product which was purified by chromatography to give the title product.

Workup

  1. customthe mixture reaction
  2. customQuenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-878d0cf0f3354885bd4f201d046954ab
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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