4-Hydroxybiphenyl → HCID 11118365, compound

HRID 1709845Notes

Reaction equation

HRID 1709845 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.Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][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

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 11118365HCID 11118365, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 34 g (0.2 mole) of 4-phenylphenol, 63 g (0.4 mole) of 1-bromo-3-chloropropane and 82.9 g (0.6 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 17 hr. The mixture was cooled, filtered, and the filtrate concentrated under reduced pressure. The residue was triturated with petroleum ether (30°-60° C.) and a solid crystallized. The solid was collected by filtration and was subjected to flash chromatography on 400 g of silica gel on a 10-cm diameter column to remove starting phenol. The column was eluted with a 1:2 mixture of benzene and cyclohexane, and fractions containing title compound were combined and concentrated to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and dried to yield 35.1 g (71%) of title compound as a white solid. An analytical sample was recrystallized from petroleum ether (60°-110° C.), mp 65°-66° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was triturated with petroleum ether (30°-60° C.)
  7. customa solid crystallized
  8. filtrationThe solid was collected by filtration
  9. customto remove
  10. washThe column was eluted with a 1:2 mixture of benzene and cyclohexane, and fractions
  11. additioncontaining title compound
  12. concentrationconcentrated
  13. customto give a solid residue
  14. customThe solid was triturated with petroleum ether (30°-60° C.)
  15. filtrationcollected by filtration
  16. customdried

Sources & evidence

ORD record
ord-8e3d4ce9ca594d84845b2826f322441a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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