Process for the alkylation of α, β-unsaturated aldehydes

Claim 1

A process for preparing at least one aldehyde represented by the structure: ##STR14## comprising the step of intimately admixing a halide having the structure R 1 X wherein X is chloro with an unsaturated aldehyde having the structure: ##STR15## in the presence of an alkali metal hydroxide, an inert solvent and a "phase transfer agent", wherein one of the dashed lines is a double bond and the other of the dashed lines is a single bond; wherein R 1 is prenyl or benzyl, R 2 is methyl, n-propyl, 4-methyl-3-pentenyl or n-hexyl, and R 3 and R 4 are each the same or different and are hydrogen, methyl or ethyl with the proviso that when R 3 is methyl or ethyl the dashed line between the beta carbon atom and the gamma carbon atom represents a double bond and when R 3 is hydrogen, either of the dashed lines is a double bond; said phase transfer agent having the structure: ##STR16## wherein at least one of the groups R' 1 , R' 2 , R' 3 and R' 4 is C 6 -C 14 alkaryl or C 6 -C 20 alkenyl, and the other of R' 1 , R' 2 , R' 3 and R' 4 is C 1 -C 8 alkyl, and Z represents halogen, the temperature of the reaction being in the range of from about 10° up to about 150° C, the mole ratio of unsaturated aldehyde:halide being from 0.5:1.5 up to about 1.5:0.5, the mole ratio of alkali metal hydroxide:halide being from about 0.75:1 up to about 1.5:1 and the concentration of "phase transfer agent" in grams per mole of unsaturated aldehyde being from 0.5 up to 25.