Sodium Carbonate → 3-Methyl-2-(pent-2-ynyl)-cyclopent-2-enone
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
Product 1
Reagents, catalysts & solvents 1
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 %).