The Syntheses of 4,4′-(1,n-Dioxaalkane)-bisbenzaldehydes and 4,4′-(1,n-Dioxaalkane)-bis(α-methoxy Phenylacetic Acids)

The syntheses of 4,4′-(1,n-dioxaalkane)-bis(α-methoxyphenylacetic acids) were conducted using a base-catalyzed reaction. The reactants were potassium hydroxide (or lithium hydroxide/lithium chloride), bromoform, methanol and 4,4′-(1,n-dioxaalkane)-bisbenzaldehydes. The aldehyde starting materials were prepared using the Williamson ether synthesis, by condensing p-hydroxybenzaldehyde and 1,n-dibromoalkanes with lithium hydride in ethanol. The effect of varying the hydrocarbon length in the dioxaalkane bridge unit is a significant consideration (the number of CH 2 units in the bridge varying from two to eight) in their acid salt formation. † Current address: D-54Z, R-13, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-4000.