Journal of the American Chemical Society

Epoxyethers. XI. O→ O Acyl Migrations with α-Hydroxyacylals

CL Stevens, BT Gillis

Index: Stevens; Gillis Journal of the American Chemical Society, 1957 , vol. 79, p. 3448,3449

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Citation Number: 44

Abstract

CH, CH, O'\ C/ CHa XI11 IX a-Chloroisobutyraldehyde (I) yielded 82% of a- hydroxyisobutyraldehyde dimethylacetal (11) when allowed to react with sodium methoxide in excess methanol for 1.5 hr. at 50'. The structure of I1 was proved by preparation of its solid 3, 5-dinitrobenzoate derivative 111, hydrolysis of the acetal to the aldehyde IV, followed by oxidation to the acid V. This acid was converted to an amide VI which was prepared ...