Water → 1~3~,1~5~,2~5~,3~3~,3~5~-Pentamethyl[1~1~,2~1~:2~3~,3~1~-terphenyl]-2~2~-ol

HRID 733028Notes

Reaction equation

HRID 733028 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=2)[C:5]([O:16]C)=[C:4]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[CH:3]=1.O.C(OCC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)[C:5]([OH:16])=[C:6]([C:8]2[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 687435442~2~-Methoxy-1~3~,1~5~,2~5~,3~3~,3~5~-pentamethyl-1~1~,2~1~:2~3~,3~1~-terphenyl

Product 1

HCID 687422881~3~,1~5~,2~5~,3~3~,3~5~-Pentamethyl[1~1~,2~1~:2~3~,3~1~-terphenyl]-2~2~-olYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 1 mL of water and 4 mL of dimethoxyethane was added into a flask into which 2,6-dibromo-4-methylanisole (400 mg, 1.43 mmol), 3,5-dimethylphenylboronic acid (658 mg, 4.39 mmol), palladium acetate (14 mg, 0.062 mmol), triphenylphosphine (60 mg, 0.23 mmol), and potassium phosphate (940 mg, 4.43 mmol) were already added, and then refluxed at normal temperature for 6 hours. After cooling to normal temperature, an ammonium chloride aqueous solution (5 mL) and 10 mL of diethylether were added thereto to separate an organic layer and extract residues using diethylether. The separated organic layer was dried with magnesium sulfate and volatile materials were removed to produce 453 mg of white 4-methyl-2,6-bis(3′,5′-dimethylphenyl)anisole solid (yield 96%). The anisole thus produced was dissolved in 5 mL of methylene chloride without separate purification, 3 mL of boron tribromide (1 M methylene chloride solution) were dropped thereonto at −78° C., and the reaction was carried out while the temperature was slowly increased to normal temperature. After the reaction, a mixed solution of water (5 mL) and diethylether (10 mL) was added to separate an organic layer and extract an aqueous solution layer using diethylether (5 mL×3), and the separated organic layer was dried. Residues from which volatile components were removed at reduced pressure were purified using a silica gel chromatography tube in a mixed solvent of hexane and methylene chloride to produce 0.41 g of white 4-methyl-2,6-bis(3′,5′-dimethylphenyl)phenol solid.

Workup

  1. customwithout separate
  2. custompurification, 3 mL of boron tribromide (1 M methylene chloride solution)
  3. additionwere dropped
  4. customat −78° C.
  5. temperaturewas slowly increased to normal temperature
  6. customAfter the reaction
  7. customto separate an organic layer
  8. extractionextract an aqueous solution layer
  9. customthe separated organic layer was dried
  10. customResidues from which volatile components were removed at reduced pressure
  11. customwere purified

Sources & evidence

ORD record
ord-c9cc9b9703d04bc5b3b26c5764a4e20e
Source dataset
uspto-grants-2009_09
Patent number
US07589042B2

Reaction notes

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