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

HRID 2204435Notes

Reaction equation

HRID 2204435 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.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C.C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

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

Product 1

HCID 22133700HCID 22133700, compoundYield 165.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

40.0 g (235 mmol) of 2-phenylphenol from Tokyo Chemical Industry Co., Ltd. and 51.06 g (282 mmol) of 6-bromo-1-hexanol from Tokyo Chemical Industry Co., Ltd. were dissolved in 600 mL of methyl ethyl ketone from Kanto Chemical Co., Inc. to prepare a solution. 97.4 g of sodium carbonate were added to the solution, and refluxed for 8 hrs. After the solution was cooled to have room temperature, it was filtered and condensed. The resultant light brown liquid was dissolved in methylene chloride and washed with water. The isolated organic layer was dried with magnesium sulfide and a solvent was removed therefrom. The residue was refined by silica gel column chromatography using methylene chloride as an eluent to obtain 105.3 g of 6-(2-phenyl-phenoxy)hexane-1-ol.

Workup

  1. customto prepare a solution
  2. temperaturerefluxed for 8 hrs
  3. temperatureAfter the solution was cooled
  4. customto have room temperature
  5. filtrationit was filtered
  6. customcondensed
  7. washwashed with water
  8. dry with materialThe isolated organic layer was dried with magnesium sulfide
  9. customa solvent was removed

Sources & evidence

ORD record
ord-c48f0b5a93544dec905fec507004e7e3
Source dataset
uspto-grants-2016_06
Patent number
US09365670B2

Reaction notes

Loading…