4-Nitrobenzaldehyde → 2,2-Dimethyl-5-[(4-nitrophenyl)methylidene]-1,3-dioxane-4,6-dione

HRID 1256922Notes

Reaction equation

HRID 1256922 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C)C=CC=CC=1.[CH3:19][C:20]1([CH3:28])[O:27][C:25](=[O:26])[CH2:24][C:22](=[O:23])[O:21]1.N1CCCCC1>C(O)(=O)C>[CH3:19][C:20]1([CH3:28])[O:27][C:25](=[O:26])[C:24](=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:22](=[O:23])[O:21]1

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 1140TolueneHCID 8082PiperidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 8242742,2-Dimethyl-5-[(4-nitrophenyl)methylidene]-1,3-dioxane-4,6-dioneYield 69.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 4-nitrobenzaldehyde (15.1 g) were added a toluene (180 mL) solution, Meldrum's acid (14.4 g), piperidine (300 μL) and acetic acid (300 μL) at room temperature, and the mixture was stirred for 5 hr. Insoluble material was collected by filtration, and the obtained solid was washed with ethyl acetate (80 mL). The resulting precipitate was collected by filtration to give the title compound (19.3 g) as a pale-yellow solid.

Workup

  1. filtrationInsoluble material was collected by filtration
  2. washthe obtained solid was washed with ethyl acetate (80 mL)
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-73520dfa6d5345e1ba031d845663de3f
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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