Water → 2-(2,3,6-Trifluorophenyl)ethan-1-ol

HRID 1722297Notes

Reaction equation

HRID 1722297 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[CH2:16][C:17](O)=[O:18].O.[OH-].[Na+]>C(OCC)C>[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[CH2:16][CH2:17][OH:18]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27779482,3,6-Trifluorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 148346752-(2,3,6-Trifluorophenyl)ethan-1-olYield 102.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Lithium aluminum hydride (0.8 g) is suspended in dry diethyl ether (5 ml) and the mixture is stirred. To the mixture is added dropwise a solution of 2-(2,3,6-trifluorophenyl)acetic acid (2.0 g) in dry diethyl ether (15 ml), and the mixture is refluxed for 30 minutes. To the reaction mixture are added water (0.8 ml), 10% aqueous sodium hydroxide (0.8 ml) and water (1.6 ml) in this order, and the mixture is stirred at room temperature. To the mixture is added diethyl ether (10 ml), and the resulting precipitates are separated by filtration and washed with tetrahydrofuran. The washing liquid and the filtrate are combined and then concentrated under reduced pressure to give 2-(2,3,6-trifluorophenyl)ethyl alcohol (1.9 g), as colorless oil.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. stirringthe mixture is stirred at room temperature
  3. customthe resulting precipitates
  4. customare separated by filtration
  5. washwashed with tetrahydrofuran
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f692048de14b4b98986effd3d6741f0f
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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