4-Hydroxybiphenyl → HCID 476768, compound

HRID 269709Notes

Reaction equation

HRID 269709 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+].Cl[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>CN(C)C=O.O>[OH:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][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

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanol

Product 1

HCID 476768HCID 476768, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

17 g of 4-phenylphenol (0.1 mol) was dissolved in 120 mL of N,N-dimethylformamide (hereafter abbreviated as DMF), 15.2 g of potassium carbonate powder (0.11 mol) was added with constant stirring, and the mixture was then stirred for one hour while heating at 90° C. Subsequently, 6-chloro-1-hexanol (14.3 g, 0.11 mol) was added dropwise to the mixture, and the reaction was allowed to proceed for 12 hours under constant stirring. Following confirmation by gas chromatography that the peaks derived from the raw materials had disappeared, the reaction mixture was diluted with water, and the precipitated solid was recovered by filtration. The resulting solid was then recrystallized from ethanol, yielding 23 g of 4-(6-hydroxyhexyloxy)phenylbenzene (yield: 85%).

Workup

  1. additionwas added with constant stirring
  2. waitto proceed for 12 hours under constant stirring
  3. filtrationthe precipitated solid was recovered by filtration
  4. customThe resulting solid was then recrystallized from ethanol

Sources & evidence

ORD record
ord-40f6c336f8404548bd058465e843450d
Source dataset
uspto-grants-2008_11
Patent number
US07449223B2

Reaction notes

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