3,4-Dichlorophenylacetic acid → 2-(3,4-Dichlorophenyl)ethanol

HRID 1677840Notes

Reaction equation

HRID 1677840 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16](O)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14]>C(OCC)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH2:15][CH2:16][OH:17]

Participants

4

Reactant 2

HCID 798743,4-Dichlorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2445582-(3,4-Dichlorophenyl)ethanolYield 101%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of lithium aluminum hydride (7.79 g, 195 mmol) in anhydrous diethyl ether (435 mL) was added slowly as a powder, via a solid dropping funnel, 3,4-dichlorophenyl acetic acid (27.20 g, 130 mmol). When the addition was completed, the reaction mixture was refluxed for 12 hours. The reaction was quenched by cautious addition of saturated sodium sulfate aqueous solution (20 mL), the resulting insoluble was then filtered off and the filtrate was concentrated in vacuo to yield 25.09 g of the desired alcohol.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture was refluxed for 12 hours
  3. customThe reaction was quenched by cautious addition of saturated sodium sulfate aqueous solution (20 mL)
  4. filtrationthe resulting insoluble was then filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6d9bb934406b4acca67fa9a8ec424e21
Source dataset
uspto-grants-2011_08
Patent number
US08008342B2

Reaction notes

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