4-Hydroxybiphenyl → HCID 21281389, compound

HRID 414615Notes

Reaction equation

HRID 414615 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:3][C:2]([O:1][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 561724HCID 561724, compound

Product 1

HCID 21281389HCID 21281389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-hydroxybiphenyl (34 g), 1-(p-toluenesulfonyloxy)-6-chlorohexane (60 g), anhydrous potassium carbonate (60 g) and dimethylformamide (400 ml) was stirred at 60° C. for 6 hours. Excess potassium carbonate was removed by filtration. Water and ethyl acetate were then added and the resultant solution washed with water, dried with magnesium sulfate and evaporated. The resulting crude residue was then dissolved in ethyl acetate/hexane and recrystallized to yield 1-(4-biphenyloxy)-6-chlorohexane.

Workup

  1. customExcess potassium carbonate was removed by filtration
  2. additionWater and ethyl acetate were then added
  3. washthe resultant solution washed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. dissolutionThe resulting crude residue was then dissolved in ethyl acetate/hexane
  7. customrecrystallized

Sources & evidence

ORD record
ord-90d759b3a1ab4455bfab99c947cd9b85
Source dataset
uspto-grants-1988_12
Patent number
US04792570

Reaction notes

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