Acrylonitrile → 4,4-Diphenyl-4-formylbutanenitrile

HRID 1602160Notes

Reaction equation

HRID 1602160 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](#[N:19])[CH:17]=[CH2:18].N12CCCN=C1CCCCC2>O1CCOCC1>[C:10]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH:8]=[O:9])[CH2:18][CH2:17][C:16]#[N:19])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 13696DiphenylacetaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 196102744,4-Diphenyl-4-formylbutanenitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of diphenylacetaldehyde (11.0 mL) and acrylonitrile (4.5 mL) in dioxane (125 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10.5 mL). The solution was heated under reflux overnight and then concentrated in vacuo. The residue was purified by a silica gel column eluting with (95:5) hexane/ethyl acetate. The desired product (8.115 g) was obtained a colorless crystals, mp 80-82° C.: MS showed (M+NH4)+ @ 267; 1H-NMR (CDCl3, δ): 2.05-2.15 (m, 2H), 2.65-2.75 (m, 2H). 7.11-7.45 (m, 10 H), 9.80 (s, 1H); Anal. Calcd for C17HI5NO: C, 81.90; H, 6.60; N, 5.61. Found: C, 81.83; H, 6.64; N, 5.65.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column
  5. washeluting with (95:5) hexane/ethyl acetate

Sources & evidence

ORD record
ord-5b04f767e2fe46e0b9ec9a72d2c627b0
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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