Water → 2-[(6-Chlorohexyl)oxy]-1,1′-biphenyl

HRID 2118662Notes

Reaction equation

HRID 2118662 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]OS(C1C=CC(C)=CC=1)(=O)=O.[OH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:21]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]([O:19][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 561724HCID 561724, compound

Product 1

HCID 201928952-[(6-Chlorohexyl)oxy]-1,1′-biphenyl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-6-(p-toluenesulphonyloxy)hexane (100 g), 2-hydroxybiphenyl (59 g) and potassium carbonate (60 g) were heated with stirring in dimethylformamide at 70° for 16 hours. The solution was cooled and added to water, then extracted with ether. The extract was washed with water, dried and evaporated, and the residue was chromatographed on silica gel (1800 g) eluting with 99:1 hexane; ethyl acetate, so as to afford the title compound as an oil.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customthe residue was chromatographed on silica gel (1800 g)
  7. washeluting with 99:1 hexane

Sources & evidence

ORD record
ord-4d15e15712ac4425a3cf055e8cfe13fe
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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