Methyl iodide → HCID 86754811, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2E,4E) and (2Z,4E)-2-bromo-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoic acid (75 g) was dissolved in dimethylformamide (500 ml) and slowly added to a suspension of sodium hydride (10.5 g; 65% in oil) in tetrahydrofuran (1100 ml) at 10° C. and then stirred until all hydrogen evolution ceased. Methyl iodide (50 g) was then added and the resulting mixture was heated for 2 hours at 50-60° C., poured onto an ice-water mixture and extracted with hexane. The hexane extracts were washed with water, dried (magnesium sulphate) and concentrated. The mixture of methyl esters was then separated by HPLC (2.5% ether/hexane) to give pure methyl (2Z,4E)-2-bromo-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoate (20 g) and methyl (2E,4E)-2-bromo-3-methyl-5-(2,6,6-trimethyl-cyclohexen-1-yl)-2,4-pentadienoate (37 g).

Provenance & Evidence