Acetic Acid → HCID 367495, compound

HRID 1494402Notes

Reaction equation

HRID 1494402 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=[O:13].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.C(OCC)C.O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:11]([C:12]([CH3:14])=[O:13])[C:10]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 367495HCID 367495, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

8.69 g (7×10-2 mol) of p-fluorobenzaldehyde, 9.11 g (7×10-2 mol) of ethyl acetoacetate, 0.24 g (2.8×10-3 mol) of piperidine and 0.84 g (1.4×10-2 mol) of glacial acetic acid were dissolved in 40 ml of dry benzene dehydrated by molecular sieve, and the mixture was refluxed under heating at 100° C. for about 3 hours for azeotropically removing water. After confirming the disappearance of the starting materials by thin layer chromatography, the reaction solution was cooled to room temperature, and 50 ml of ethyl ether was added thereto. The mixture was washed three times with 100 ml of water and twice with 100 ml of a saturated sodium chloride aqueous solution. The ether solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure by an evaporator. The residual oil was left to stand overnight in a refrigerator. The solid thereby obtained was recrystallized from hexane to obtain 14.08 g (yield: 85.2%) of slightly yellow prism crystals. Melting point: 80°-82° C.

Workup

  1. temperaturethe mixture was refluxed
  2. washThe mixture was washed three times with 100 ml of water
  3. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure by an evaporator
  5. waitThe residual oil was left
  6. customThe solid thereby obtained
  7. customwas recrystallized from hexane
  8. customto obtain 14.08 g (yield: 85.2%) of slightly yellow prism crystals

Sources & evidence

ORD record
ord-772f19e2176048b5a15b8f4e16ca06f4
Source dataset
uspto-grants-1991_06
Patent number
US05026708

Reaction notes

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