Acetic Acid → HCID 54394445, compound

HRID 1649407Notes

Reaction equation

HRID 1649407 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([O:15][C:16](=[O:22])[CH2:17][C:18]([CH2:20][Cl:21])=[O:19])[CH3:14].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.C(OCC)(=O)C.O>[CH2:13]([O:15][C:16](=[O:22])[C:17](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[C:2]([F:12])([F:11])[F:1])[C:18](=[O:19])[CH2:20][Cl:21])[CH3:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 69484Ethyl 4-chloroacetoacetateHCID 123067o-(Trifluoromethyl)benzaldehyde

Product 1

HCID 54394445HCID 54394445, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

226.2 g of 2-trifluoromethylbenzaldehyde, 235 g of 4-chloroacetoacetic acid ethyl ester, 4.2 ml of glacial acetic acid and 2.1 ml of piperidine were dissolved in 500 ml of benzene and the solution was boiled for 8 hours using a water separator. 1 liter of ethyl acetate was added and the mixture was extracted twice with sodium bicarbonate, once with citric acid and once more with water, dried and evaporated. The crude product was subjected to incipient distillation up to 130° under a high vacuum and the product remained as the residue in the form of a chromatographically pure 2:1 isomer mixture.

Workup

  1. extractionthe mixture was extracted twice with sodium bicarbonate, once with citric acid and once more with water
  2. customdried
  3. customevaporated
  4. distillationdistillation up to 130° under a high vacuum

Sources & evidence

ORD record
ord-85ee7e34f0d54f7a9091983282f06b17
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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