3-Cyanobenzoic acid → 3-(Hydroxymethyl)benzonitrile

HRID 2242244Notes

Reaction equation

HRID 2242244 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].B.C1COCC1>C1COCC1>[OH:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[C:1]#[N:2]

Participants

4

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 27346773-(Hydroxymethyl)benzonitrileYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyanobenzoic acid (5 g, 34.0 mmol) was dissolved in THF (50 mL) at ambient temperature. To this solution was added borane/THF complex (1M in THF, 68 mL, 68.0 mmol) in three portions and borane trifluoride/diethyl etherate complex (4.3 mL, 34.0 mmol). The reaction mixture was stirred at ambient temperature for 2 hours, quenched with methanol and stirred for 10 minutes. The solution was diluted with ethyl acetate and washed with saturated NaHCO3 (3×). The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2.19 g, 48% yield) as a solid.

Workup

  1. customquenched with methanol
  2. stirringstirred for 10 minutes
  3. additionThe solution was diluted with ethyl acetate
  4. washwashed with saturated NaHCO3 (3×)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00655a0f11514d9fa18e68660e06c52d
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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