1-Naphthaldehyde → 1-(2-nitroprop-1-enyl)naphthalene

HRID 399641Notes

Reaction equation

HRID 399641 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=O)[C:4]2=[CH:3][CH:2]=1.[N+:13]([CH2:16][CH3:17])([O-:15])=[O:14]>C(O)C.CO.C(N)CCC>[C:10]1([CH:11]=[C:16]([N+:13]([O-:15])=[O:14])[CH3:17])[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 61951-NaphthaldehydeHCID 6587Nitroethane

Product 1

HCID 7088071-(2-nitroprop-1-enyl)naphthaleneYield 90%

Reagents, catalysts & solvents 3

HCID 8007ButylamineCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 1-naphthylaldehyde (624.8 g, 4.0 mol), nitroethane (300.0 g, 4 mol) and n-butylamine (14.8 g, 0.20 mol) was refluxed in ethanol (400 mL) for 24 hours. The mixture was cooled, diluted with methanol (200 mL), and filtered to give 767 g (90% yield) of 1-naphthyl-2-nitropropene. Upon standing, an additional 60 g (97% total yield) of 1-naphthyl-2-nitropropene crystallized from solution.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-3eac0cc036414685a127f2a40c9cae2b
Source dataset
uspto-grants-1998_10
Patent number
US05821387

Reaction notes

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