Cyclododecanemethanol → Cyclododecanecarboxaldehyde

HRID 37298

Reaktionsgleichung

Reaktionsgleichung von HRID 37298
[CH:1]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[Na+].Cl[O-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH:1]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

8

Edukt 5

HCID 74686CyclododecanemethanolHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 78737CyclododecanecarboxaldehydeAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 9.92 g (50 mmol) of cyclododecane methanol in 100 ml of methylene chloride under a nitrogen atmosphere is added 50 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO) and 510 mg (5 mmol) of sodium bromide in 5 ml of water. The solution is cooled to 10°-15° C. and a solution of 100 ml of 5.25% aqueous sodium hypochlorite and 2.0 g of sodium bicarbonate is added over 1 hour. The reaction mixture is allowed to warm to room temperature and after 1 hour is diluted with methylene chloride. The organic phase is washed with aqueous sodium thiosulfate, aqueous bicarbonate and water. The methylene chloride layer is dried over magnesium sulfate, filtered and evaporated in vacuo to give 9.43 g of crude title compound as an oil: IR (film) 1723 cm-1 ; NMR (CDCl3)) δ 1.34 (bs, 18H), 1.41 (m, 4H), 1.54 (m, 2H), 1.65 (m, 2H), 2.40 (m, 1H), 9.64 (d, 1H, J=1.6 Hz) M+ (EI) 196.

Aufarbeitung

  1. temperatureThe solution is cooled to 10°-15° C.
  2. washThe organic phase is washed with aqueous sodium thiosulfate, aqueous bicarbonate and water
  3. dry with materialThe methylene chloride layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-38da7748ad104fcca20b5b9611834741
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420153

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