Ammonium Chloride → 2-(3-Fluorophenyl)ethanol

HRID 1590602Notes

Reaction equation

HRID 1590602 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1.[Cl-].[NH4+]>CCOCC>[F:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][OH:16])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 676173-Fluorophenylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5731322-(3-Fluorophenyl)ethanolYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred suspension of lithium aluminium hydride (25 g, 0.65 mol) in dry ether (300 ml) at 0° C. was added dropwise 3-fluorophenylacetic acid (50 g, 0.32 mol, Lancaster Synthesis). After the addition the mixture was heated to reflux for 2 hours, then stirred overnight at room temperature. Saturated aqueous ammonium chloride (200 ml) was added and the mixture was filtered and the solids washed with ether. The ether layer was separated, dried over anhydrous magnesium sulphate and evaporated. Distillation of the residue afforded 2-(3-fluorophenyl)ethanol (43.05 g, 95%), bp 91°-94° at 2 mmHg, NMR δ 7.3 (1H, m), 7.05-6.9 (3H, m), 3.85 (2H,t), 2.85 (2H,t), 2.0 (1H,s).

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureto reflux for 2 hours
  4. filtrationthe mixture was filtered
  5. washthe solids washed with ether
  6. customThe ether layer was separated
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c7e289861f344ab7b2c89ddb363ee2e9
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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