Triphenylsilanol → (2,6,6-Trimethyl-4-oxocyclohex-2-en-1-ylidene)acetaldehyde

HRID 1460830

Reaktionsgleichung

Reaktionsgleichung von HRID 1460830
C1([Si](C2C=CC=CC=2)(C2C=CC=CC=2)[OH:8])C=CC=CC=1.[CH3:21][C:22]1[C:27](O)([C:28]#[CH:29])[C:26]([CH3:32])([CH3:31])[CH2:25][C:24](=[O:33])[CH:23]=1>C1(C)C(C)=CC=CC=1.[V].C(O)(=O)CCCCCCCCCCCCCCCCC>[CH3:21][C:22]1[C:27](=[CH:28][CH:29]=[O:8])[C:26]([CH3:32])([CH3:31])[CH2:25][C:24](=[O:33])[CH:23]=1

Komponenten

6

Edukt 2

HCID 69925TriphenylsilanolHCID 578890HCID 578890, Verbindung

Produkt 1

HCID 53790600(2,6,6-Trimethyl-4-oxocyclohex-2-en-1-ylidene)acetaldehydeAusbeute 365,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5281Stearic AcidKatalysatorHCID 23990VanadiumKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

Triphenylsilanol (22 g) and 80 g (0.45 mol) of 3,5,5-trimethyl-4-hydroxy-4-ethynylcyclohex-2-en-1-one and 1.6 g of stearic acid are dissolved in 800 ml of xylene, treated with 1.92 ml of vanadium isopropylate and heated to reflux temperature while stirring. After 31/2 hours the reaction mixture is cooled and washed with 5% sodium bicarbonate, whereby an emulsion results. The organic phase is then separated, the emulsion is also separated and extracted with ether. The organic phases are dried over magnesium sulphate and concentrated. The residue (117.9 g) is distilled (oil bath 130°-170°; 0.001 mm Hg). In this manner there are obtained 51.8 g (64.8%) of (2,6,6-trimethyl-4-oxo-2-cyclohexen-1-ylidene)acetaldehyde (Z:E=about 3:1).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux temperature
  3. temperatureAfter 31/2 hours the reaction mixture is cooled
  4. washwashed with 5% sodium bicarbonate, whereby an emulsion
  5. customresults
  6. customThe organic phase is then separated
  7. customthe emulsion is also separated
  8. extractionextracted with ether
  9. dry with materialThe organic phases are dried over magnesium sulphate
  10. concentrationconcentrated
  11. distillationThe residue (117.9 g) is distilled (oil bath 130°-170°; 0.001 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-df58c5fc2fb048dfb99c08bf4e1c387a
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05072019

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