m-Formylbenzonitrile → 3-(Hydroxymethyl)benzonitrile

HRID 1866892Notes

Reaction equation

HRID 1866892 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].CO.C1COCC1.[BH4-].[Na+]>[Cl-].[Na+].O>[OH:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 4311764Sodium borohydrideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 27346773-(Hydroxymethyl)benzonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice-cold solution of 3-cyanobenzaldehyde (5.0 g, 38 mmol) in 1:1 MeOH/THF (90 mL) was added NaBH4 (1.6 g, 42 mmol), and the reaction mixture was stirred for 3 h. The reaction mixture was diluted with brine, and the solvent was removed under reduced pressure. The residue was dissolved in water, and the aqueous layer was extracted with Et2O (3×100 mL). The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to provide 3-hydroxymethyl-benzonitrile (4.95 g, 98%) as a clear oil, which was used in the next step without further purification or characterization.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionthe aqueous layer was extracted with Et2O (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c3d9be869ca4336952b3dbc0ae1b555
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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