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

HRID 2070545Notes

Reaction equation

HRID 2070545 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>C1(C)C=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

6

Reactant 4

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

Product 1

HCID 290662Spiro(4.5)decan-6-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of potassium tert-butoxide (22.4 g) in toluene (120 mL) was added a solution of cyclohexanone (9.82 g) and 1,4-dibromobutane (21.6 g) in toluene (30 mL) while stirring, followed by stirring the reaction mixture at 95° C. for 3.5 hours. After cooling down to room temperature and adding ice-cold water (100 mL) and 2N aqueous hydrochloric acid solution (50 mL) to the reaction mixture, the organic layer was separated. Then, after the aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with saturated brine, dried and concentrated. The residue was distilled in vacuo (90 to 100° C./3 to 4 mmHg) to give spiro[4.5]decan-6-one (7.85 g).

Workup

  1. stirringby stirring the reaction mixture at 95° C. for 3.5 hours
  2. customthe organic layer was separated
  3. extractionThen, after the aqueous layer was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. distillationThe residue was distilled in vacuo (90 to 100° C./3 to 4 mmHg)

Sources & evidence

ORD record
ord-60c7dc9db07a45039355590469aaa8f8
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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