Hydrochloric Acid → Spiro(4.5)decan-6-one

HRID 539929Notes

Reaction equation

HRID 539929 reaction equation
CC(C)([O-])C.[K+].[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:15][CH2:16][CH2:17][CH2:18]Br.Cl>CC(O)(C)C.C1C=CC=CC=1>[CH2:15]1[C:8]2([CH2:9][CH2:10][CH2:11][CH2:12][C:7]2=[O:13])[CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 80561,4-DibromobutaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 290662Spiro(4.5)decan-6-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

In a flask containing potassium tert-butoxide (45.7 g, 407.6 mmol) in t-BuOH (200 mL) and Benzene (150 mL) was added cyclohexanone (20.0 g, 203.8 mmol) and 1,4-dibromobutane (44.0 g, 203.8 mmol). The solution was heated at 120° C. for 6 hrs. The mixture was cooled to room temperature and neutralized with HCl (1N). The solution was extracted with ether, dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude residue was purified by silica gel chromatography (1% EtOAc/hexanes) to afford the title compound: GCMS ES+=153.1.

Workup

  1. extractionThe solution was extracted with ether
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude residue was purified by silica gel chromatography (1% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3d15c87822b74046a76472b31baf51e3
Source dataset
uspto-grants-2014_10
Patent number
US08871774B2

Reaction notes

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