Benzenepropanal → 2-Hydroxy-4-phenylbutanenitrile

HRID 2290506Notes

Reaction equation

HRID 2290506 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(O)[O-].[Na+].[C-:16]#[N:17].[Na+]>O.C(O)C>[OH:10][CH:9]([CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:16]#[N:17]

Participants

6

Reactant 3

HCID 7707BenzenepropanalHCID 8929Sodium CyanideHCID 23665763Sodium Bisulfite

Product 1

HCID 109098692-Hydroxy-4-phenylbutanenitrileYield 47.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

3-Phenylpropionaldehyde (0.40 mole) was added dropwise to a solution of sodium bisulfite (0.80 mole) in 240 mL water and 50 mL 95% ethanol at room temperature over a 30 min period. A solution of sodium cyanide (0.40 mole) in 60 mL water was added dropwise to the stirred white suspension over a 20 min period at room temperature. After continuing stirring for an additional 2 hrs, the reaction mixture was extracted with ether (4×250 mL). The extracts were combined, dried (MgSO4) and concentrated in vacuo to give 30.4 g (47%) of 2-hydroxy-4-phenylbutyronitrile as a viscous pale yellow oil.

Workup

  1. extractionthe reaction mixture was extracted with ether (4×250 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb91d92d9b6a42edb07b1b7006fcd75a
Source dataset
uspto-grants-1986_10
Patent number
US04617291

Reaction notes

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