Acetone → O-Terphenyl

HRID 1803652Notes

Reaction equation

HRID 1803652 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)CC.OCC(C)(CO)C.CC(C)=O>CC(O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]1([C:7]2[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 7095BiphenylHCID 31344Neopentyl glycolHCID 4100861(4-Propylphenyl)boronic acid

Product 1

HCID 6766O-TerphenylYield 89%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of (2 mmol) of 8, (2.2 mmol) of 4-propylphenylboronic acid, 250 mg (2.40 mmol) of neopentyl glycol, 1:53 g (4.84 mmol) of Ba(OH)2. 8H2O, 1.35 ml (0.103 mmol, 5 mol %) of a 76 mM acetone solution of Pd(OAc)2 in 20 ml of 95% i-PrOH is stirred at 80° for 12 hours. The solvent is subsequently removed under reduced pressure. 5 ml of 2 M HCl are added to the residue, and the mixture is extracted with dichloromethane (3×5 ml). The combined organic phases are dried over MgSO4 and filtered through SiO2. The solvent is removed under reduced pressure, and the residue is converted into 10 (yield: 89%).

Workup

  1. customThe solvent is subsequently removed under reduced pressure
  2. addition5 ml of 2 M HCl are added to the residue
  3. extractionthe mixture is extracted with dichloromethane (3×5 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. filtrationfiltered through SiO2
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9c394195aedf4dc29903eadebc6e5abe
Source dataset
uspto-grants-2013_01
Patent number
US08350100B2

Reaction notes

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