Hydrochloric Acid → Spiro(5.5)undecan-1-one

HRID 12046

Reaction equation

HRID 12046 reaction equation
Br[C:2](Br)([CH2:5][CH3:6])[CH2:3][CH3:4].[C:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[K].C([O-])(C)(C)C.Cl>C1(C)C=CC=CC=1>[C:8]1(=[O:14])[C:13]2([CH2:6][CH2:5][CH2:2][CH2:3][CH2:4]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 135557303,3-DibromopentaneHCID 50987170Potassium tertbutoxide

Product 1

HCID 573924Spiro(5.5)undecan-1-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dibromopentane (5 mmol) is added to a solution of cyclohexanone (5 mmol) and potassium-tert-butanolate (10 mmol) in toluene (7.5 ml) and the reaction mixture is refluxed for 48 hours. After cooling to room temperature 25% hydrochloric acid is added and extraction is carried out with diethyl ether. The combined organic phases produce, after drying over sodium sulphate, removal of the solvent in a vacuum and chromatography of the residue using silica gel (ethyl acetate/heptane, 1:5) pure spiro[5.5]undecan-1-one (Tetrahedron 1964, 20, 2553-2573): tR 1.90 min. (LC-2); ESI-MS (+): m/z 167.27 [M+H]+.

Workup

  1. temperaturethe reaction mixture is refluxed for 48 hours
  2. additionis added
  3. extractionextraction
  4. customThe combined organic phases produce
  5. dry with materialafter drying over sodium sulphate, removal of the solvent in a vacuum and chromatography of the residue

Sources & evidence

ORD record
ord-dc56b055e1544a4a8c8c799f73e8849d
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Linked notes

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