Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile

HRID 1951394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1951394
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].C(O)(=O)C.N1CCCCC1>ClCCl.C1CCCCC1.C(OCC)(=O)C>[C:15]([C:14]([C:13](=[O:18])[CH3:12])=[CH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1])(=[O:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 122905503-Chloro-4-formylbenzonitrile

Produkt 1

HCID 674168404-(2-Acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrileAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 21867204Cyclohexane ethylacetateLösungsmittel

Versuchsvorschrift

300 mg (1.812 mmol) of 3-chloro-4-formylbenzonitrile, 181.4 mg (1.812 mmol) of 2,4-pentanedione, 163.2 mg (2.72 mmol) of acetic acid and 30.9 mg (0.36 mmol) of piperidine are dissolved in 15 ml of dichloromethane and heated under reflux with an inverse water trap overnight. The mixture shows complete conversion (TLC check, mobile phase: cyclohexane/ethyl acetate 5:1). The mixture is diluted with dichloromethane, washed with water and saturated sodium chloride solution and dried with sodium sulfate. The solvent is removed in a rotary evaporator. 403 mg (89.8% of theory) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-chlorobenzonitrile are obtained and are reacted without further purification.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customThe solvent is removed in a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-8344fbcb2ebf436692eb2bcd4f9543bb
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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