(4-Chlorophenoxy)acetic acid → 2-(4-Chlorophenoxy)ethanol

HRID 260344

Reaction equation

HRID 260344 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14](O)=[O:15])=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 26229(4-Chlorophenoxy)acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 159072-(4-Chlorophenoxy)ethanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask under a nitrogen atmosphere was added 6.1 g. of lithium aluminum hydride in 60 ml. of dry THF at -4° C. The resulting slurry was stirred and 20.0 g. (0.102 mole) of 4-chlorophenoxyacetic acid in 100 ml. of dry THF was added dropwise. The reaction was stirred overnight and was quenched by cautiously adding saturated aqueous sodium sulfate solution followed by ethyl acetate. The solid was removed by filtration and the aqueous phase was extracted twice with 50 ml. portions of ethyl acetate. The combined ethyl acetate solutions were washed with aqueous saturated sodium chloride solution (brine) and then dried using magnesium sulfate. Removal of the solvent resulted in 17.6 g. (94% yield) of 2-(4-chlorophenoxy)ethanol being isolated as a yellow oil.

Workup

  1. additionTo a flask under a nitrogen atmosphere was added 6.1 g
  2. customat -4° C
  3. stirringThe reaction was stirred overnight
  4. customwas quenched by cautiously adding saturated aqueous sodium sulfate solution
  5. customThe solid was removed by filtration
  6. extractionthe aqueous phase was extracted twice with 50 ml
  7. washThe combined ethyl acetate solutions were washed with aqueous saturated sodium chloride solution (brine)
  8. customdried
  9. customRemoval of the solvent
  10. customresulted in 17.6 g

Sources & evidence

ORD record
ord-a40cd8aca1a74f4eaf2956e9ef072b6c
Source dataset
uspto-grants-1996_06
Patent number
US05527816

Linked notes

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