Hydroxyamine hydrochloride → 4-Methyl-3-phenyl-4-pentenenitrile

HRID 2387599Notes

Reaction equation

HRID 2387599 reaction equation
[CH3:1][C:2](=[CH2:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][CH:5]=O.Cl.[NH2:15]O>C(O)C>[CH3:1][C:2](=[CH2:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][C:5]#[N:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 204881864-Methyl-3-phenyl-4-pentenal

Product 1

HCID 584354774-Methyl-3-phenyl-4-pentenenitrileYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methyl-3-phenyl-4-pentenal (15.27 g; 0.077 mol) and hydroxylamine hydrochloride (8.1 g; 0.116 mol) were heated together in 95% ethyl alcohol (125 ml) at reflux under nitrogen for 3 hours. Ethyl alcohol was removed on the rotavapor and the residue partitioned between n-heptane and water (100 ml each). The aqueous phase was reextracted with n-heptane (100 ml). Each organic phase was washed with 5% aqueous HCl, water, aqueous saturated NaHCO3 and brine (100 ml each). Combined extracts were dried over anhydrous sodium sulfate. The product was purified by column chromatography on silica gel (eluting with heptane/ethyl acetate 10:1 to 5:1) followed by bulb-to-bulb distillation. 4.9 g of the desired product were obtained (0.0285 mol; yield=37%).

Workup

  1. temperatureat reflux under nitrogen for 3 hours
  2. customEthyl alcohol was removed on the rotavapor
  3. customthe residue partitioned between n-heptane and water (100 ml each)
  4. washEach organic phase was washed with 5% aqueous HCl, water, aqueous saturated NaHCO3 and brine (100 ml each)
  5. dry with materialCombined extracts were dried over anhydrous sodium sulfate
  6. customThe product was purified by column chromatography on silica gel (eluting with heptane/ethyl acetate 10:1 to 5:1)
  7. distillationfollowed by bulb-to-bulb distillation

Sources & evidence

ORD record
ord-c8f55a905492427aac0100fe2272752d
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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