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

HRID 2240810Notes

Reaction equation

HRID 2240810 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 19371017Spiro[2.5]octan-6-oneYield 138.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5627b3ec797d4607a191532ede2b531e
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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