p-Toluenesulfonic acid → (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

HRID 1995158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1995158
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[C@H:3]1[C:13]([O:15]C(C)(C)C)=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:20][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[C@H:3]1[C:13]([OH:15])=[O:14]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 86739004tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

Produkt 1

HCID 12807755(1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acidAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1.4 g of the product of Step B, 100 mg of p-toluene sulfonic acid and 14 ml of toluene was stirred at 120° C. for 21/2 hours and was then evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether, was cooled and filtered. The product was dried to obtain 900 mg of (1R,cis) 2,2-dimethyl-3-[Z-2-(isopropoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid melting at 98° C.

Aufarbeitung

  1. customwas then evaporated to dryness under reduced pressure
  2. customThe residue was crystallized from isopropyl ether
  3. temperaturewas cooled
  4. filtrationfiltered
  5. customThe product was dried

Quellen und Nachweise

ORD-Eintrag
ord-808f4543eb984392a27702946e3d67f3
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04402972

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