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

HRID 970821Notes

Reaction equation

HRID 970821 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.[CH2:14](Br)[CH:15]=[CH2:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)C>[CH2:16]([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:15]=[CH2:14]

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 2579864-[(Prop-2-en-1-yl)oxy]-1,1'-biphenylYield 78.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Phenylphenol 64 (25.5 g, 0.15 mol), allyl bromide (20.0 g, 0.165 mol) and K2CO3 (41.5 g, 0.15 mol) in 75 ml of dry DMF were stirred at room temperature overnight. The reaction mixture was diluted with 500 ml of diethyl ether and washed with water. The ether layer was washed with brine, dried and concentrated to give a lightly brown solid that was recrystallized from hexane to give 24.9 g of 4-allyloxy-biphenyl 65. Step 2: 3-Allyl-biphenyl-4-ol 66.

Workup

  1. washwashed with water
  2. washThe ether layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a lightly brown solid that
  6. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-affd9e0597004eeba78b83a85b550baa
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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