The Syntheses of 4,4′-(1,n-Dioxaalkane)-bisbenzaldehydes and 4,4′-(1,n-Dioxaalkane)-bis(α-methoxy Phenylacetic Acids)
- 1 March 1998
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 28 (6) , 1041-1050
- https://doi.org/10.1080/00397919808003072
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.Keywords
This publication has 5 references indexed in Scilit:
- The crystal structures of rubidium and sodium acid salts of α-methoxy-α-phenylacetic acidActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1980
- Reactions of Aryl Trichloromethyl Carbinols with NucleophilesSynthesis, 1971
- The infrared spectra and studies of the structures of alkali acid salt complexes of α-methoxyphenylacetic acidSpectrochimica Acta Part A: Molecular Spectroscopy, 1970
- The Synthesis of α-Methoxyarylacetic Acids from the Base-catalyzed Condensation of Arylaldehydes with Bromoform and Methanol. Studies of Aldehyde ReactivitiesJournal of the American Chemical Society, 1961
- The Synthesis of α-Methoxyarylacetic Acids from the Base-catalyzed Condensation of Arylaldehydes with Haloforms and MethanolJournal of the American Chemical Society, 1960