Methyl Ethyl Ketone → HCID 476768, compound

HRID 1464837Notes

Reaction equation

HRID 1464837 reaction equation
C(C(C)=O)C.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:13]1([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:12][CH:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanol

Product 1

HCID 476768HCID 476768, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 80 mL of methyl ethyl ketone, 9.05 g (50 mmol) of 4-hydroxybiphenyl, 10.20 g (60 mmol) of 6-bromo-1-hexanol, and 20.7 g (150 mmol) of potassium carbonate were added. This solution was refluxed for 24 hours and then cooled to room temperature. This solution was diluted with 200 mL of methylene chloride and rinsed with water three times. The organic phase was then separated and dried over magnesium sulfate, and the solvent was distilled off. The residue was dissolved in toluene and purified by recrystallization to provide 10.25 g of 6-(4-phenylphenoxy)hexane-1-ol.

Workup

  1. temperatureThis solution was refluxed for 24 hours
  2. washrinsed with water three times
  3. customThe organic phase was then separated
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off
  6. dissolutionThe residue was dissolved in toluene
  7. custompurified by recrystallization

Sources & evidence

ORD record
ord-9e95a0e347ad4af396770b69ab968504
Source dataset
uspto-grants-2015_04
Patent number
US08998400B2

Reaction notes

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