Hydrochloric Acid → HCID 53665973, compound

HRID 1902993Notes

Reaction equation

HRID 1902993 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)C=O.N1CCCCC1.[C:31](O)(=O)[CH2:32][C:33]([OH:35])=[O:34].Cl>N1C=CC=CC=1>[Cl:24][C:16]1[CH:17]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:19]=[C:2]([Cl:1])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:31]=[CH:32][C:33]([OH:35])=[O:34])[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 13050449HCID 13050449, compound

Product 1

HCID 53665973HCID 53665973, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

270 g of 5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-benzaldehyde and 6 g of piperidine were added, at 25° C., to 89.5 g of malonic acid in 570 ml of pyridine. The reaction mixture was stirred for 5 hours at 85° to 90° C. and was then heated for 90 minutes under reflux, after which it was poured onto water, the mixture was acidified with hydrochloric acid and the product was filtered off. The crystalline product was recrystallized from n-butanol. 200 g (66% of theory) of 3-(5-(2,6-dichloro-4-trifluoromethyl-phenoxy)-2-nitrophenyl)-propenoic acid, of melting point 192° C., were obtained in the form of yellow crystals.

Workup

  1. temperaturewas then heated for 90 minutes
  2. temperatureunder reflux
  3. additionafter which it was poured onto water
  4. filtrationthe product was filtered off
  5. customThe crystalline product was recrystallized from n-butanol

Sources & evidence

ORD record
ord-b0495d6cb3f74b3786c7c1acc9c8655d
Source dataset
uspto-grants-1984_03
Patent number
US04435208

Reaction notes

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