Acrylonitrile → 4,4-Diphenyl-4-formylbutanenitrile

HRID 1781493Notes

Reaction equation

HRID 1781493 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>C(O)(C)C>[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 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Diphenylacetaldehyde (25.6 g), acrylonitrile (12.5 ml), and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU:2.5 g) were stirred in isopropyl alcohol (250 ml) with warming at 70° C. for 6 hours. The reaction mixture was concentrated to dryness and the group was purified by silica gel column chromatography. The crude crystal crop obtained was washed with isopropyl ether to provide the title compound (19.8 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe group was purified by silica gel column chromatography
  3. customThe crude crystal crop obtained
  4. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-559dde09b3ed44a1952c44f127de01bf
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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