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

HRID 1272039Notes

Reaction equation

HRID 1272039 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)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture of dry THF (20 ml) and 1.0 M lithiumaluminiumhydride (9.0 ml, 9.0 mmol) was placed under an atmosphere of nitrogen. A solution of 4-chlorophenoxyacetic acid (1.9 g, 10 mmol) in dry THF (10 ml) is slowly added dropwise. When addition was complete the reaction mixture was stirred for 30 min and then heated at reflux temperature for 10 min. The cooled reaction mixture was quenched with small amounts of water and 4 N NaOH and ethyl acetate was added. The mixture was dried (MgSO4) and then concentrated. The residue was re-evaporated with DCM to give crude 2-(4-chlorophenoxy)ethanol as an oil.

Workup

  1. additionWhen addition
  2. temperatureheated
  3. temperatureat reflux temperature for 10 min
  4. customThe cooled reaction mixture
  5. customwas quenched with small amounts of water and 4 N NaOH and ethyl acetate
  6. additionwas added
  7. dry with materialThe mixture was dried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was re-evaporated with DCM

Sources & evidence

ORD record
ord-41aa256d8b5748bba94e9351882d5ec8
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

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