Hydroxyamine hydrochloride → (E)-4-methyl-5-p-tolylpent-4-enenitrile

HRID 2408257Notes

Reaction equation

HRID 2408257 reaction equation
[CH3:1]/[C:2](=[CH:7]\[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)/[CH2:3][CH2:4][CH:5]=O.Cl.[NH2:16]O>C(O)C>[CH3:1]/[C:2](=[CH:7]\[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)/[CH2:3][CH2:4][C:5]#[N:16]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 714656444-Pentenal, 4-methyl-5-(4-methylphenyl)-, (4E)-

Product 1

HCID 58390602(E)-4-methyl-5-p-tolylpent-4-enenitrileYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4E)-4-methyl-5-(4-methylphenyl)-4-pentenal (3.2 g, 0.017 mol) and hydroxylamine hydrochloride (1.77 g, 0.025 mol) were heated together in 95% ethyl alcohol (55 ml) at reflux for 4 hours. After cooling to room temperature, ethanol was removed on the rotavapor. The residue was stirred in diethyl ether (250 ml) for 30 minutes. The solid was filtered off, rinsed with diethyl ether and discarded. The filtrate was evaporated under vacuum. The product was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate 11:1) followed by bulb-to-bulb distillation. 2.18 g of the desired compound were obtained (0.012 mol, 70% yield).

Workup

  1. temperatureat reflux for 4 hours
  2. customethanol was removed on the rotavapor
  3. filtrationThe solid was filtered off
  4. washrinsed with diethyl ether
  5. customThe filtrate was evaporated under vacuum
  6. customThe product was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate 11:1)
  7. distillationfollowed by bulb-to-bulb distillation

Sources & evidence

ORD record
ord-d9ed61a99fb04ea088e6347f2f564dc0
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

Loading…