Sodium Hydroxide → Spiro-[2.5]octan-6-one

HRID 2240810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240810
[CH2:1]1[C:3]2([CH2:12][CH2:11][C:6]3(OCC[O:7]3)[CH2:5][CH2:4]2)[CH2:2]1.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O.C(O)(C(F)(F)F)=O>[CH2:2]1[C:3]2([CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]2)[CH2:1]1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 573366227,10-Dioxadispiro[2.2.4~6~.2~3~]dodecane

Produkt 1

HCID 19371017Spiro-[2.5]octan-6-oneAusbeute 138,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7,10-dioxa-dispiro[2.2.4.2]dodecane (6.25 g, approx. 29 mmol) in THF (25 mL), water (20 mL) and TFA (10 mL) is stirred at rt for 2 h. The mixture is neutralized by adding 2 N aq. NaOH and sat. NaHCO3 solution and extracted with diethyl ether. The organic extracts are washed with water, dried over Na2SO4, filtered and the solvent of the filtrate is removed to give spiro[2.5]octan-6-one (5.0 g) as a colourless oil containing remainders of toluene (product volatile). 1H NMR (CDCl3): δ 2.14 (t, J=6.4 Hz, 4H), 1.40 (t, J=6.4 Hz, 4H), 0.21 (s, 4H).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe organic extracts are washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent of the filtrate is removed

Quellen und Nachweise

ORD-Eintrag
ord-5627b3ec797d4607a191532ede2b531e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723378B2

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