p-Toluenesulfonic acid → 1-[4-Chloro-2-(methanesulfonyl)phenyl]-3-cyclopropylpropane-1,3-dione

HRID 2256946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2256946
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([CH:8]([C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])C(OC(C)(C)C)=O)=[O:7])=[C:4]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6](=[O:7])[CH2:8][C:16]([CH:18]2[CH2:19][CH2:20]2)=[O:17])=[C:4]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:3]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 53638759HCID 53638759, Verbindung

Produkt 1

HCID 545513651-[4-Chloro-2-(methanesulfonyl)phenyl]-3-cyclopropylpropane-1,3-dioneAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of t-butyl 2-(4-chloro-2-methylsulphonylbenzoyl)-3-cyclopropyl-3-oxopropionate (9.5 g) and 4-toluenesulphonic acid (1.5 g) in toluene was stirred and heated at reflux for 3 hours. After cooling the mixture was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 1-(4-chloro-2-methylsulphonylphenyl)-3-cyclopropylpropan-1,3-dione, (7.1 g) as an orange gum, NMR (CDCl3): 0.8-1.2 (m, 4H), 1.5-1.9 (m, 1H), 3.3 (s, 3H), 5.8 (s, 1H), 7.3-7.6 (m,2H), 7.9 (s, 1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the mixture
  4. washwas washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-22bd7b2f391248d6890402ad965d712b
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656573

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