3-Nitrobenzaldehyde → 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-[(3-nitrophenyl)methylene]-

HRID 864319Notes

Reaction equation

HRID 864319 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 5403981,3-Dioxane-4,6-dione, 2,2-dimethyl-5-[(3-nitrophenyl)methylene]-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(3-Nitrobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione can be obtained in the following manner: a solution of 30.2 g of 3-nitrobenzaldehyde and 2,2-dimethyl-1,3-dioxane-4,6-dione in 400 cm3 of dimethylformamide is stirred for 18 hours at a temperature near to 20° C. The reaction mixture is diluted with 500 cm3 of ethyl acetate, washed five times with water, dried over magnesium sulphate, filtered and concentrated to dryness (1.2 kPa) to give an oil. This oil is crystallized in 100 cm3 of ethanol to give 26 g of 5-(3-nitrobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione in the form of a solid melting at 128° C.

Workup

  1. washwashed five times with water
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness (1.2 kPa)
  5. customto give an oil
  6. customThis oil is crystallized in 100 cm3 of ethanol

Sources & evidence

ORD record
ord-4cf72d53d3aa428a9f60f914f607b707
Source dataset
uspto-grants-1996_10
Patent number
US05563136

Reaction notes

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