Dimethyl Sulfide → (1-Ethoxyethoxy)acetaldehyde

HRID 34728

Reaktionsgleichung

Reaktionsgleichung von HRID 34728
[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=C)[CH3:5])[CH3:2].[O:10]=[O+][O-].CSC.C([O-])([O-])=O.[K+].[K+]>O.CCOCC.CO>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH:8]=[O:10])[CH3:5])[CH3:2]

Komponenten

8

Edukt 4

HCID 1068Dimethyl SulfideHCID 11430Potassium CarbonateHCID 24823OzoneHCID 127395961-Allyloxyethoxyethane

Produkt 1

HCID 13876797(1-Ethoxyethoxy)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

3-[1-(Ethoxy)ethoxy]-1-propene (40 g., 0.0307 mol) was stirred in 100 ml. methanol at -78° for 5.5 hours as O3 was through the solution. The resulting pale blue solution was purged with H2, dimethyl sulfide (34 ml., 43.4 g., 0.68 mol) was added, and the mixture warmed to room temperature over 45 minutes. K2CO3 (0.2 g.) was added, the reaction mixture stripped of solvent, and the residue diluted with 1:1 water:ether. The aqueous layer was separated, diluted with brine and extracted with fresh ether. The organic layers were combined, dried and stripped to yield the title product as an oil, 15.25 g., 1H-nmr: 1.24 (t, 3H), 1.37 (d, 3H), 3.50 (s, 2H), 3.61 (m, 2H), 4.81 (m, 1H), 9.87 (s, 1H).

Aufarbeitung

  1. additionwas added
  2. customThe aqueous layer was separated
  3. additiondiluted with brine
  4. extractionextracted with fresh ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4e654396608144d388e441b765cdac51
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762921

Verknüpfte Notizen

Wird geladen…