Methanol → 4-(1-Hydroxyethyl)benzonitrile

HRID 2059734Notes

Reaction equation

HRID 2059734 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].CO.[BH4-].[Na+]>C1COCC1>[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 3

HCID 887MethanolHCID 740444'-CyanoacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 5833354-(1-Hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Acetylbenzonitrile (3 g, 20.67 mmol) was dissolved in THF (5 mL) and MeOH (5 mL) and cooled to 0° C. NaBH4 (0.782 g, 20.67 mmol) was added slowly. The reaction aged at rt for 30 min and was concentrated. 2M aq HCl was added and the solution was extracted with EtOAc. The organic layer was washed with water, dried with Na2SO4, filtered and concentrated to provide the product.

Workup

  1. concentrationwas concentrated
  2. addition2M aq HCl was added
  3. extractionthe solution was extracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide the product

Sources & evidence

ORD record
ord-44fe43f1ced14970afa942b80192800b
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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