Benzyl Alcohol → Propanenitrile, 3-(phenylmethoxy)-

HRID 539964Notes

Reaction equation

HRID 539964 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:12])[CH:10]=[CH2:11].Cl>[OH-].[Na+]>[CH2:1]([O:8][CH2:11][CH2:10][C:9]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 7855Acrylonitrile

Product 1

HCID 80620Propanenitrile, 3-(phenylmethoxy)-Yield 93.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of benzyl alcohol (108 g, 1 mol) and 40% aqueous solution of sodium hydroxide (10 mL) was added prop-2-enenitrile (58.3 g, 1.1 mol) and the mixture was stirred for 6 hours at room temperature. The mixture was neutralized with 1 N hydrochloric acid, and extracted with dichloromethane (300 mL). The organic layer was washed with 5% solution of sodium hydroxide (300 mL) and brine (300 mL), dried over sodium sulfate and concentrated in vacuo to afford 150 g of the desired compound (yield was 93%).

Workup

  1. extractionextracted with dichloromethane (300 mL)
  2. washThe organic layer was washed with 5% solution of sodium hydroxide (300 mL) and brine (300 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-065715ccc3114e82a901fcfb2c77d921
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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