Cycloheptylbenzene → 4-Cycloheptyl-benzaldehyde

HRID 1579108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579108
[CH:1]1([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2C=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2C=CC=CC=2)CCCCCC1.Cl[CH:30]([O:32]C(Cl)Cl)Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([C:8]2[CH:9]=[CH:12][C:13]([CH:30]=[O:32])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 297933CycloheptylbenzeneHCID 558102Bis(dichloromethyl) etherHCID 21484447Cycloheptylbenzaldehyde

Produkt 1

HCID 214844454-Cycloheptyl-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Cycloheptylbenzaldehyde can be manufactured as follows: 200 ml of titanium tetrachloride are added dropwise, whilst stirring, to a solution of 200 g of cycloheptylbenzene in 600 ml of absolute methylene chloride under a nitrogen atmosphere at -10°C, and thereafter 132.5 g of dichloromethyl ether are added similarly at 0°C. The reaction mixture is then stirred for a further 30 minutes at 10°C and poured onto 3 kg of ice, and the whole is extracted twice with 500 ml of methylene chloride. The organic phases are washed with water, dried over sodium sulphate and evaporated to dryness in vacuo. Distillation of the evaporation residue in a high vacuum yields 4-cycloheptyl-benzaldehyde in the fraction boiling at 120-130°C/0.8 mm Hg.

Aufarbeitung

  1. extractionthe whole is extracted twice with 500 ml of methylene chloride
  2. washThe organic phases are washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness in vacuo
  5. distillationDistillation of the evaporation residue in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a5a5efb5cbef40bfa593d8b3e3171f90
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03940434

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