Hexane → Cyclopentylidenecyclopentan-2-one

HRID 1266001Notes

Reaction equation

HRID 1266001 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].C[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[C:10]1(=[C:2]2[CH2:3][CH2:4][CH2:5][C:1]2=[O:6])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 8452CyclopentanoneHCID 14797Potassium Hydroxide

Product 1

HCID 69995Cyclopentylidenecyclopentan-2-oneYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of cyclopentanone (336.5 g, 4.0 moles) in absolute ethanol (500 mL) at room temperature was added KOH (5.6 g, 0.1 mole) in one portion. The reaction was stirred at room temperature for 65 hours. The reaction was determined to be completed by TLC and GC analyses. Hexane was added to the reaction mixture and the layers were separated. The organic layer was washed successively with 10% HCl (aqueous), saturated NaHCO3 (aqueous) and brine. The resulting organic layer was dried with MgSO4, filtered, and concentrated. The brown oil was distilled under vacuum to give 2-cyclopentylidenecyclopentan-1-one (155 g, 52% yield). The structural formula of 2-cyclopentylidenecyclopentan-1-one is shown in FIG. 1.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed successively with 10% HCl (aqueous), saturated NaHCO3 (aqueous) and brine
  3. dry with materialThe resulting organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe brown oil was distilled under vacuum

Sources & evidence

ORD record
ord-b5970edb721340e8af36571d3fcfa220
Source dataset
uspto-grants-2003_04
Patent number
US06548474B1

Reaction notes

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