(1,1'-Biphenyl)-2-ol → HCID 22133700, compound

HRID 1483861Notes

Reaction equation

HRID 1483861 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>C(C(C)=O)C>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 10340Sodium CarbonateHCID 779706-Bromo-1-hexanol

Product 1

HCID 22133700HCID 22133700, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Seventy-eight point five (78.5) g (461 mmol) of 2-phenylphenol from Tokyo Chemical Industry Co., Ltd. were dissolved in 600 mL of methyl ethyl ketone from Kanto Chemical Co., Inc. to prepare a solution. One hundred ninety one (191) g (1.38 mol) of sodium carbonate from Kanto Chemical Co., Inc. and 100 g (553 mmol) of 6-bromo-1-hexanol from Tokyo Chemical Industry Co., Ltd. were added to the solution, and refluxed for 8 hrs. After the solution was cooled to have room temperature, it was filtered and a solvent was removed therefrom. The residue was dissolved in methylene chloride from Junsei Chemical Co., Ltd. and washed with water. The isolated organic layer was dried with magnesium sulfide from Kanto Chemical Co., Inc., and a solvent was removed therefrom. The residue was refined by silica gel column chromatography using a mixed solvent in which a volume ratio of methylene chloride from Junsei Chemical Co., Ltd. to methanol from Kanto Chemical Co., Inc. is 99/1 as an eluent to obtain 105.3 g of 6-(2-phenyl-phenoxy)hexane-1-ol.

Workup

  1. customto prepare a solution
  2. additionwere added to the solution
  3. temperaturerefluxed for 8 hrs
  4. temperatureAfter the solution was cooled
  5. customto have room temperature
  6. filtrationit was filtered
  7. customa solvent was removed
  8. dissolutionThe residue was dissolved in methylene chloride from Junsei Chemical Co
  9. washand washed with water
  10. dry with materialThe isolated organic layer was dried with magnesium sulfide from Kanto Chemical Co
  11. custom, and a solvent was removed

Sources & evidence

ORD record
ord-ae2fdabac5044110a07dfe6ce2258107
Source dataset
uspto-grants-2016_08
Patent number
US09416284B2

Reaction notes

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