4-Hydroxybiphenyl → HCID 53649217, compound

HRID 1377911Notes

Reaction equation

HRID 1377911 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC(C)=O.BrCCCCC(OC)=O>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerate

Product 1

HCID 53649217HCID 53649217, compoundYield 116.8%

Reagents, catalysts & solvents 2

HCID 79557Methyl 5-bromovalerateCatalystHCID 180AcetoneSolvent

Procedure

A mixture in acetone of 4-phenylphenol (0.85 g, 5.0 mmol) and potassium carbonate (0.76 g, 5.5 mmol) was stirred for 30 minutes. Neat methyl 5-bromovalerate (0.78 mL, 5.5 mmol) was added dropwise via syringe and the reaction mixture was stirred for 2 hours at ambient temperature and overnight at reflux. Catalytic KI was then added and the reaction mixture was heated overnight at reflux. An additional 10 drops of methyl 5-bromovalerate was then added and reflux was continued for 8 hours. The reaction mixture was cooled to ambient temperature and filtered. The collected solid was washed with acetone and the combined filtrate and washings were concentrated in vacuo. The residue was partitioned between ethyl ether and water. The aqueous phase was extracted with ethyl ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give 5-(4-phenylphenoxy)pentanoic acid methyl ester (1.66 g) as a white powder.

Workup

  1. temperatureat reflux
  2. additionCatalytic KI was then added
  3. temperaturethe reaction mixture was heated overnight
  4. temperatureat reflux
  5. temperaturereflux
  6. waitwas continued for 8 hours
  7. temperatureThe reaction mixture was cooled to ambient temperature
  8. filtrationfiltered
  9. washThe collected solid was washed with acetone
  10. concentrationthe combined filtrate and washings were concentrated in vacuo
  11. customThe residue was partitioned between ethyl ether and water
  12. extractionThe aqueous phase was extracted with ethyl ether
  13. dry with materialThe combined organic layers were dried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59a7aa9dccc94baa929da6ba4db5d0e9
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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