Cyclohexanone → Spiro(5.5)undecan-1-one

HRID 2070580

Reaction equation

HRID 2070580 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][CH2:19]Br>C1(C)C=CC=CC=1>[C:7]1(=[O:13])[C:12]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 81001,5-DibromopentaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 573924Spiro(5.5)undecan-1-oneYield 65.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of potassium tert-butoxide (24.4 g) in toluene (100 mL) was added a solution of cyclohexanone (10.67 g) and 1,5-dibromopentane (25 g) in toluene (50 mL) while stirring. The mixture was stirred at 100° C. for 4 hours. After cooling down to room temperature, the resulting solid was filtered and washed with toluene. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15) to give spiro[5.5]undecan-1-one (11.85 g).

Workup

  1. stirringThe mixture was stirred at 100° C. for 4 hours
  2. filtrationthe resulting solid was filtered
  3. washwashed with toluene
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15)

Sources & evidence

ORD record
ord-8308357151d441059f21afd1306cb7f6
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Linked notes

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