Sodium Carbonate → 3-Methyl-2-(2-pentyn-1-yl)-2-cyclopenten-1-one

HRID 267304Notes

Reaction equation

HRID 267304 reaction equation
C[CH:2]1[CH2:7][CH2:6][C:5](=O)[C:4](Cl)([CH2:9][C:10]#[C:11][CH2:12][CH3:13])[C:3]1=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:5][C:6]1[CH2:7][CH2:2][C:3](=[O:15])[C:4]=1[CH2:9][C:10]#[C:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21556769HCID 21556769, compound

Product 1

HCID 126821983-Methyl-2-(2-pentyn-1-yl)-2-cyclopenten-1-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4-Methyl-2-chloro-2-(pent-2-ynyl)-cyclohexane-1,3-dione (3 g; 0.015 Mole) in dry xylene (15 ml) was allowed to reflux in the presence of anhydrous sodium carbonate (1.6 g; 0.015 Mole) until gas evolution ceased (3 h.). The reaction mixture was then washed with water, dried over magnesium sulfate and the solvent removed under reduced pressure. Distillation afforded 3-methyl-2-(pent-2-ynyl)-cyclopent-2-enone (dehydrojasmone); b.p. 80°-90°/0.001 Torr; 850 mg (35 %).

Workup

  1. custom(3 h.)
  2. washThe reaction mixture was then washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. distillationDistillation

Sources & evidence

ORD record
ord-5db4ad7ef17045c8b3fa802cb2777fc0
Source dataset
uspto-grants-1976_03
Patent number
US03941828

Reaction notes

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