4'-Cyanoacetophenone → 4-(1-Hydroxyethyl)benzonitrile

HRID 572590Notes

Reaction equation

HRID 572590 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[OH:3][CH:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 740444'-CyanoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 5833354-(1-Hydroxyethyl)benzonitrileYield 113.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Acetylbenzonitrile (2.0 g; 13.8 mmol) was dissolved in THF (10 mL) and MeOH (10 mL). Sodium borohydride (782 mg; 20.7 mmol) was added portionwise at 0° C. and the reaction was let stirred at RT for 40 min. Solvents were removed under vacuum, EtOAC was added, and the organic phases were washed with H2O, dried over MgSO4, filtered and concentrated affording the title compound as a colorless oil (2.3 g, quantitative). HPLC (Method A) Rt 4.31 min (Purity: 99.2%).

Workup

  1. customSolvents were removed under vacuum, EtOAC
  2. additionwas added
  3. washthe organic phases were washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4d6c6b7ef8ec498aa9bad1112e0ed9d5
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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