Aluminium lithium hydride → HCID 58197372, compound

HRID 1503399Notes

Reaction equation

HRID 1503399 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[C:9]([CH2:18][CH2:19][OH:20])=[C:10]([CH:14]=[CH:15][C:16]=1[F:17])[C:11](O)=[O:12]>C1COCC1>[F:7][C:8]1[C:16]([F:17])=[CH:15][CH:14]=[C:10]([CH2:11][OH:12])[C:9]=1[CH2:18][CH2:19][OH:20]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58197315HCID 58197315, compound

Product 1

HCID 58197372HCID 58197372, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (2.45 g, 0.065 mol) in THF (30 mL) was added 3,4-difluoro-2-(2-hydroxyethyl)benzoic acid (8.7 g, 0.043 mol) in THF (60 mL) at 0° C. The mixture was stirred at room temperature overnight. The reaction was quenched with 3 mL of H2O, followed by aqueous NaOH solution (3 mL, 10%). The solution was filtered and the filtrated was concentrated to give the residue, which was purified by chromatography to give 2-(2,3-difluoro-6-(hydroxymethyl)phenyl)ethanol (2.5 g, 31%). 1H NMR (CDCl3): 2.99 (m, 2H), 3.58 (s, 2H), 3.83 (t, 2H), 4.52 (s, 2H), 7.03 (m, 2H).

Workup

  1. customThe reaction was quenched with 3 mL of H2O
  2. filtrationThe solution was filtered
  3. concentrationthe filtrated was concentrated
  4. customto give the residue, which
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-799b750ee7714dee871dc5300994f593
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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