Water → 2-Propenenitrile, 3-(4-fluorophenyl)-

HRID 596783

Reaction equation

HRID 596783 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=O)=[CH:4][CH:3]=1.C([O-])=O.[Na+].Cl.[NH2:17]O.O>C(O)=O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 533843793-(4-Fluorophenyl)-2-propenal

Product 1

HCID 3673242-Propenenitrile, 3-(4-fluorophenyl)-Yield 70.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

p-Fluorocinnamaldehyde (9.0 g.) was refluxed for 1 hr. in 98% formic acid containing sodium formate (10 g.) and hydroxylamine hydrochloride (7 g.). The solution was cooled and poured into water (275 ml.), giving a solid. This was washed well with water, leaving p-fluorocinnamonitrile (6.21 g., 70%), m.p. 64°-65°, λmax. (EtOH) 271 nm ε 22500.

Workup

  1. temperatureThe solution was cooled
  2. customgiving a solid
  3. washThis was washed well with water

Sources & evidence

ORD record
ord-e9949bbebf3b423f8e3963e521514c62
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Linked notes

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