Sodium Hydroxide → 2-(4-Fluorophenoxy)ethanol

HRID 1895921Notes

Reaction equation

HRID 1895921 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][CH2:13][C:14](OC(C)(C)C)=[O:15])=[CH:10][CH:9]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[F:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67118384Tert-butyl 2-(4-fluorophenoxy)acetate

Product 1

HCID 5743612-(4-Fluorophenoxy)ethanolYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (378 mg, 10.0 mmol) was added at −15° C. to a solution of tert-butyl 2-(4-fluorophenoxy)acetate (2.03 g, 9.00 mmol) in tetrahydrofuran (10 ml) and stirred at room temperature for 20 minutes. Aqueous 15% NaOH solution (2 ml), Na2SO4 (2.84 g) and H2O (6 ml) were added to the reaction mixture and stirred for 1 hour. The resulting precipitation was filtered off and washed with tetrahydrofuran (30 ml×3). The filtrate was dried over Na2SO4, filtered and concentrated in vacuo to give 2-(4-fluorophenoxy)ethanol (1.12 g, 80%) as yellow oil: LC-MS: 157 [M+1]+.

Workup

  1. stirringstirred for 1 hour
  2. customThe resulting precipitation
  3. filtrationwas filtered off
  4. washwashed with tetrahydrofuran (30 ml×3)
  5. dry with materialThe filtrate was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7053fdd32cb4861a509e00a2efcdfd1
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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