2,6-Dichlorophenylacetic acid → 2-(2,6-Dichlorophenyl)ethanol

HRID 1677844Notes

Reaction equation

HRID 1677844 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH2:15][C:16](O)=[O:17]>C(OCC)C>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH2:15][CH2:16][OH:17]

Participants

4

Reactant 2

HCID 810582,6-Dichlorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27341002-(2,6-Dichlorophenyl)ethanolYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

a suspension of lithium aluminum hydride (13.75 g, 365.75 mmol) in anhydrous diethyl ether (500 mL) was added via a powder addition funnel 2,6-dichlorophenylacetic acid (50 g, 243.75 mmol). The resulting reaction mixture was refluxed for 16 hours and then quenched by slow addition of a sodium sulfate saturated aqueous solution (25 mL). The resulting slurry was stirred for 3 hours and then filtered, the insoluble was carefully washed with diethyl ether (2×100 mL). The combined ether filtrates were dried over sodium sulfate and the solvent was evaporated in vacuo to yield 38.6 g (85% yield) of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 16 hours
  3. customquenched by slow addition of a sodium sulfate saturated aqueous solution (25 mL)
  4. filtrationfiltered
  5. washthe insoluble was carefully washed with diethyl ether (2×100 mL)
  6. dry with materialThe combined ether filtrates were dried over sodium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0afb276c64cf4dd48406c9c98c93fe12
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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