Sodium sulfate decahydrate → [3-(2,4-Dimethylphenyl)phenyl]methanol

HRID 273378Notes

Reaction equation

HRID 273378 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](OCC)=[O:16])[CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23111852Ethyl 2',4'-dimethyl[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 23111675[3-(2,4-Dimethylphenyl)phenyl]methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2′,4′-dimethylbiphenyl-3-carboxylate (5.0 g, 19.7 mmol) in anhydrous tetrahydrofuran (50 mL) was added lithium aluminum hydride (0.91 g, 24.0 mmol) under ice-cooling and the mixture was stirred at room temperature for 3 hrs. The reaction solution was ice-cooled and sodium sulfate 10 hydrate (8.0 g, 24.8 mmol) was added. The mixture was stirred at room temperature for 1 hr. The precipitated insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound as a colorless oil (yield 96%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringThe mixture was stirred at room temperature for 1 hr
  4. filtrationThe precipitated insoluble material was filtered off through celite
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88c0d71d81454d459e5d07356b7fbd2b
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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