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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 6
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Original Articles

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

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Pages 1041-1050 | Received 01 Sep 1997, Published online: 20 Aug 2006
 

Abstract

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 CH2 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.

Notes

Current address: D-54Z, R-13, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-4000.

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