Selenium Dioxide → 2-(p-Chlorobenzoyl)-benzaldehyde

HRID 328678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 328678
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([OH:15])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][OH:14])=[CH:4][CH:3]=1.[Se](=O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]=[O:14])=[O:15])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 197815594'-Chloro-2-hydroxymethylbenzhydrol

Produkt 1

HCID 199363582-(p-Chlorobenzoyl)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 18.6 g. of 4'-chloro-2-hydroxymethylbenzhydrol in 100 ml. of acetic acid and 10.4 g. selenium dioxide was refluxed for 2 hours. The mixture was poured on ice and made alkaline and extracted with ether. Concentration of the ether solution and addition of petroleum ether gave pale yellow prisms which after recrystallization from a mixture of ether and petroleum ether gave 2-(p-chlorobenzoyl)-benzaldehyde melting at 112°-113°. Ultraviolet inflexion (2-propanol) at 225 μ (ε = 17,500) and maximum at 259 μ (ε = 22,500), infrared absorption (CHCL3) at 1670 cm-1 and 1705 cm-1.

Aufarbeitung

  1. additionThe mixture was poured on ice
  2. extractionextracted with ether
  3. additionConcentration of the ether solution and addition of petroleum ether
  4. customgave pale yellow prisms which
  5. customafter recrystallization
  6. additionfrom a mixture of ether and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-709c0c144ae94caaa289b9d403638d13
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018765

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