2,5-Cyclohexadiene-1,4-dione, 2,5-diphenyl- → [1,1':4',1''-Terphenyl]-2',5'-diol

HRID 2288254Notes

Reaction equation

HRID 2288254 reaction equation
[C:1]1([C:7]2[C:8](=[O:20])[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[O:13])[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]1([C:10]2[CH:9]=[C:8]([OH:20])[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][C:11]=2[OH:13])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 700552,5-Cyclohexadiene-1,4-dione, 2,5-diphenyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 72859[1,1':4',1''-Terphenyl]-2',5'-diolYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To dry THF was dissolved 0.5 g/1.9 mmol of 2,5-diphenylbenzoquinone in argon atmosphere, and 85 mg/2.24 mmol of lithium aluminum hydride was added to the solution. After stirring at room temperature for 30 minutes, the reaction solution was added to ice containing 1N hydrochloric acid, and the mixture was allowed to stand for 30 minutes. The aqueous layer was extracted with ethyl acetate once, and the extract was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica, gel column chromatography using hexane-methylene chloride for the eluting solution to obtain 0.28 g of the desired 2,5-diphenyl-1,4-dihydroxybenzene. 1H-NNR (CDCl3 +DMSO-d6): δ 4.52 (2H, br), 6.91 (2H, s), 7.33 (6H, m), 7.61 (4H, m).

Workup

  1. additionwas added to the solution
  2. waitto stand for 30 minutes
  3. extractionThe aqueous layer was extracted with ethyl acetate once
  4. dry with materialthe extract was dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica, gel column chromatography

Sources & evidence

ORD record
ord-be746d0e51ad4feb929ef6feb1610b50
Source dataset
uspto-grants-2000_07
Patent number
US06087502

Reaction notes

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