Benzene → 4-Hydroxy-6-methyl-3-(4-nitrophenyl)acryloyl-2-pyrone

HRID 1870951Notes

Reaction equation

HRID 1870951 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].N1CCCCC1.C1C=CC=CC=1.[CH3:24][C:25]1[O:32][C:30](=[O:31])[CH:29]([C:33]([CH3:35])=[O:34])[C:27](=[O:28])[CH:26]=1>O>[OH:28][C:27]1[CH:26]=[C:25]([CH3:24])[O:32][C:30](=[O:31])[C:29]=1[C:33](=[O:34])[CH:35]=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 5414-NitrobenzaldehydeHCID 8082PiperidineHCID 122903Dehydroacetic acid

Product 1

HCID 1354060594-Hydroxy-6-methyl-3-(4-nitrophenyl)acryloyl-2-pyroneYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitrobenzaldehyde (4.5 g, 29.7 mmol) and then a number of drops of piperidine were added to a benzene (40 ml) solution of dehydroacetic acid (5.00 g, 29.7 mmol) at room temperature, after which refluxing was performed for 6 hours while eliminating water by azeotropy. The majority of the benzene was distilled of directly, and then the distillation taken to dryness under reduced pressure. Following which, when recrystallization was performed from ethanol, 4-hydroxy-6-methyl-3-(4-nitrophenyl)acryloyl-2-pyrone (7.3 g, 82%) was obtained as orange crystals.

Workup

  1. temperatureafter which refluxing
  2. distillationThe majority of the benzene was distilled of directly, and then
  3. distillationthe distillation
  4. customwhich, when recrystallization

Sources & evidence

ORD record
ord-bdada907a2d44d15be6a7dc8e5a6fd8f
Source dataset
uspto-grants-2000_08
Patent number
US06100292

Reaction notes

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