Acetic Acid → HCID 21877053, compound

HRID 723612Notes

Reaction equation

HRID 723612 reaction equation
C(O)(=O)C.[CH3:5][C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=O>C1(C)C=CC=CC=1.N1CCCCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH:16]=[C:7]([C:6](=[O:11])[CH3:5])[C:8](=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31261AcetylacetoneHCID 357463,5-Dichlorobenzaldehyde

Product 1

HCID 21877053HCID 21877053, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

Glacial acetic acid (0.49 ml, 8.6 mmol) and piperidine (57 μL, 0.6 mmol) were added to a stirred solution of 2,4-pentanedione (2.86 g, 28.6 mmol) and 3,5-dichlorobenzaldehyde (5.00 g, 28.6 mmol) in toluene (25 ml) and the mixture was heated under reflux using a Dean-Stark trap for 18 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (10:1, by volume) to give the title compound (6.5 g) as a red/brown solid, m.p. 85–87° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customfor 18 hours
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (10:1, by volume)

Sources & evidence

ORD record
ord-7ff463ada1a044cc8d0b299e633d6dae
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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