3-Methylbenzaldehyde → m-Ethylbenzaldehyde

HRID 596528

Reaktionsgleichung

Reaktionsgleichung von HRID 596528
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[Br-].[C:11]([C:15]1[CH:40]=[CH:39][CH:38]=[CH:37][C:16]=1[CH2:17][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13]C)=[O:12].[CH3:41][C:42]1[CH:43]=[C:44]([CH:56]=[CH:57][CH:58]=1)[CH:45]=[CH:46]C1C(C(O)=O)=CC=CC=1>C(#N)C>[CH2:9]([C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[CH:7]=[O:8])[CH3:11].[CH2:45]([C:44]1[CH:43]=[C:42]([CH:58]=[CH:57][CH:56]=1)[CH:41]=[CH:17][C:16]1[C:15]([C:11]([OH:13])=[O:12])=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:46]

Komponenten

6

Edukt 3

HCID 121053-MethylbenzaldehydeHCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromideHCID 536852163'-Methylstilbene-2-carboxylic acid

Produkt 2

HCID 118623m-EthylbenzaldehydeHCID 536634343'-Ethylstilbene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

116.5 Gm. of 1,5-diazabicyclo[3.4.0]nonene-5 is added to 107.5 gm. of m-tolualdehyde and 400 gm. of o-carbomethoxybenzyltriphenylphosphonium bromide in 2000 ml. of acetonitrile. The mixture is refluxed briefly then cooled and the solvent removed under vacuum. The residue is dissolved in chloroform and washed with dilute hydrochloric acid, and the solution dried and evaporated. The product is refluxed for 11 hours in a solution of 111 gm. potassium hydroxide in 1,000 ml. of water and 150 ml. of methanol. The solution is cooled and extracted with chloroform. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with chloroform. The extract is dried and evaporated to give 177.5 gm. (91%) of 3'-methylstilbene-2-carboxylic acid (ca. 60:40 cis:trans). Use of m-ethylbenzaldehyde instead of m-tolualdehyde gives a similar yield of 3'-ethylstilbene-2-carboxylic acid.

Aufarbeitung

  1. temperatureThe mixture is refluxed briefly
  2. temperaturethen cooled
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with dilute hydrochloric acid
  6. customthe solution dried
  7. customevaporated
  8. temperatureThe product is refluxed for 11 hours in a solution of 111 gm
  9. temperatureThe solution is cooled
  10. extractionextracted with chloroform
  11. extractionextracted with chloroform
  12. customThe extract is dried
  13. customevaporated
  14. customto give 177.5 gm

Quellen und Nachweise

ORD-Eintrag
ord-c2229f3a28fe46d58904577ad22675c4
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011243

Verknüpfte Notizen

Wird geladen…