Process for producing cis-jasmone

A process for producing cis-jasmone having the structure:

• ##STR6## comprising the step of intimately admixing 3-methyl cyclopentenone-2 having the structure:
• ##STR7## with a cis pentenyl halide having the structure:
• ##STR8## in the presence of a base and a "phase transfer agent" having the generic formula:
• ##STR9## wherein at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is C.sub.6 -C.sub.14 aryl, C.sub.6 -C.sub.10 aralkyl, C.sub.6 -C.sub.20 alkyl, C.sub.6 -C.sub.14 aralkyl and C.sub.6 -C.sub.20 alkenyl and the other of R.sub.2, R.sub.3 and R.sub.4 is C.sub.1 -C.sub.8 alkyl, and Z.sup.- is an anion selected from the group consisting of halogen anion and hydroxyl anion and wherein X is chloro or bromo, said reaction being carried out in a two liquid phase system;
• the reaction temperature being in the range of from 30.degree. C up to 120.degree. C;
• the mole ratio of 3-methyl cyclopentenone-2:cis-pent-2-enyl halide being in the range of from 0.5:1.5 up to about 1.5:0.5;
• the concentration of "phase transfer agent" in the reaction mass based on the amount of 3-methyl cyclopentenone-2 being in the range of from 0.5 grams of phase transfer agent per mole of 3-methyl cyclopentenone-2 up to 25 grams of phase transfer agent per mole of 3-methyl cyclopentenone-2;
• the reaction being carried out in a solvent inert to the reaction system, selected from the group consisting of toluene, benzene, o-xylene, m-xylene, p-xylene, ethyl benzene, n-hexane and cyclohexane;
• and then fractionally distilling the resulting product whereby a residue and a distillate are formed;
• and recovering said cis-jasmone from said distillate.