Ethylene Glycol → 1-[p-(2-Thenoyl)phenyl]cyclopropanecarboxylic acid

HRID 1439593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439593
[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]#N)[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[K+].C(O)CO.C.[OH2:26]>>[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:17]([OH:26])=[O:19])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 5

HCID 174Ethylene GlycolHCID 297MethaneHCID 962WaterHCID 14797Potassium HydroxideHCID 122329781-[p-(2-Thenoyl)phenyl]cyclopropanecarbonitrile

Produkt 1

HCID 122329791-[p-(2-Thenoyl)phenyl]cyclopropanecarboxylic acid

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 10 parts of 1-[p-(2-thenoyl)phenyl]cyclopropanecarbonitrile, 3.92 parts of potassium hydroxide, 35 parts of ethylene glycol and 3.5 parts of water is stirred for 48 hours while heating at 140° C. The reaction mixture is poured onto water, stirred with activated charcoal and filtered over hyflo. The filtrate is acidified with hydrochloric acid and the product is extracted with ether. The latter is washed with water, dried, filtered and evaporated. The solid residue is crystallized from acetonitrile, yielding 6.1 parts of 1-[p-(2thenoyl)phenyl]cyclopropanecarboxylic acid; mp. 165.9° C (dec.).

Aufarbeitung

  1. additionThe reaction mixture is poured onto water
  2. filtrationfiltered over hyflo
  3. extractionthe product is extracted with ether
  4. washThe latter is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-3910d21901e04e4cb4391a37584b14f5
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04060528

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