Sodium Hydroxide → 2-Fluoro-3-methoxybenzyl alcohol

HRID 424691Notes

Reaction equation

HRID 424691 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].[OH-].[Na+]>CCOCC>[F:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 33906792-Fluoro-3-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5935892-Fluoro-3-methoxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (83.5 ml, 1M solution in THF) was added dropwise to a suspension of the subtitle product of step i) (7.1 g) in Et2O (180 ml) at a rate that maintained gentle reflux. Upon complete addition the reaction was stirred for 1.5 h. 15% sodium hydroxide solution was added dropwise until no effervescence was observed. The resulting white precipitate was filtered and the filtrate diluted with H2O (100 ml). The organics were removed in vacuo and the residue extracted with Et2O (100 ml). The organics were washed with 2M sodium hydroxide solution (150 ml), H2O (150 ml), brine (150 ml), dried (MgSO4) and concentrated in vacuo to afford the subtitle compound as a white crystalline solid. Yield: 5.5 g.

Workup

  1. temperaturemaintained gentle reflux
  2. additionUpon complete addition the reaction
  3. filtrationThe resulting white precipitate was filtered
  4. additionthe filtrate diluted with H2O (100 ml)
  5. customThe organics were removed in vacuo
  6. extractionthe residue extracted with Et2O (100 ml)
  7. washThe organics were washed with 2M sodium hydroxide solution (150 ml), H2O (150 ml), brine (150 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af22fdd2c23544c9b7480ea30da49403
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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