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

HRID 1665947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665947
[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 it 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-1f5c58949c5a4497b3443cc8f825fcec
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039644B2

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