4-Hydroxybiphenyl → HCID 13008359, compound

HRID 430862Notes

Reaction equation

HRID 430862 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.C1(=O)O[CH2:17][CH2:16][O:15]1.[OH-].[K+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][O:15][CH2:16][CH2:17][O:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 71034-HydroxybiphenylHCID 7303Ethylene carbonateHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium Hydroxide

Product 1

HCID 13008359HCID 13008359, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-Phenylphenol (34.0 g, 0.2 mole), ethylene carbonate (20.0 g, 0.227 mole) and tetrabutylammonium bromide (6.5 g, 0.02 mole) were heated to 155° C. with stirring in a three-necked, round-bottom flask equipped with a mechanical stirrer and a reflux condenser. After 5 hours, the reaction mixture was cooled to 110° C., most of the lower boiling materials were removed under reduced pressure. Finely powdered potassium hydroxide (17.0 g, 0.3 mole) was added and the reaction mixture was stirred for 5 minutes. Then, 4-chloro-benzyl chloride (35.0 g, 0.217 mole) was added and the reaction was kept at 110° C. with vigorous stirring. After 4 hours, toluene (250 ml) was added and the reaction mixture was cooled to 60° C. Water (100 ml) was added and stirring continued. Toluene layer was separated and the aqueous layer was extracted twice with warm toluene. The toluene extracts were combined, washed with water, dried and concentrated. The residue was recrystallized from toluene/methanol. Yield: 55.8 g (82%), white solid, M.P.: 85-87° C.

Workup

  1. customequipped with a mechanical stirrer and a reflux condenser
  2. customwere removed under reduced pressure
  3. stirringthe reaction mixture was stirred for 5 minutes
  4. customwas kept at 110° C. with vigorous stirring
  5. waitAfter 4 hours
  6. temperaturethe reaction mixture was cooled to 60° C
  7. stirringstirring
  8. customToluene layer was separated
  9. extractionthe aqueous layer was extracted twice with warm toluene
  10. washwashed with water
  11. customdried
  12. concentrationconcentrated
  13. customThe residue was recrystallized from toluene/methanol

Sources & evidence

ORD record
ord-07cba413962e4744a3fe5b18ddc77502
Source dataset
uspto-grants-2001_11
Patent number
US06323376B1

Reaction notes

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