Nitromethane → 4-nitro-1,3-diphenylbutan-1-one

HRID 630685Notes

Reaction equation

HRID 630685 reaction equation
[CH:1](=[CH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C(NCC)C>CO>[N+:17]([CH2:20][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 7189CinnamoylbenzeneHCID 8021Diethylamine

Product 1

HCID 2346444-nitro-1,3-diphenylbutan-1-oneYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 1 L flask, 94.7 g (0.455 mol) of benzylideneacetophenone were dissolved in 600 g of methanol, admixed with 138.9 g (2.275 mol) of nitromethane and 166.4 g (2.275 mol) of diethylamine and refluxed for 16 h. The solvent was half distilled off in vacuo and the precipitated solid was separated off and dried to constant weight in vacuo to obtain 118 g (438 mmol) of 4-nitro-1,3-diphenylbutan-1-one.

Workup

  1. temperaturerefluxed for 16 h
  2. distillationdistilled off in vacuo
  3. customthe precipitated solid was separated off
  4. customdried to constant weight in vacuo

Sources & evidence

ORD record
ord-b37301f462d643e39a5b4a56c75d255a
Source dataset
uspto-grants-2016_04
Patent number
US09317012B2

Reaction notes

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