Propanal → 1,3-Dioxan-5-ol, 2-ethyl-

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Reaction Steps

By the method of Example 27 propionaldehyde was condensed with glycerol, and the resulting intermediate was purified by the formation of the benzoate, 5-benzoyloxy-2-ethyl-1,3-dioxane, m.p. 62°-68.5° C. The benzoate was hydrolyzed by the method of Example 27 to yield 2-ethyl-5-hydroxy-1,3-dioxane, b.p. 94°-97° C/23-25 mm Hg. By the method of Example 27 the intermediate 5-hydroxy compound was converted to 5-benzyloxy-2-ethyl-1,3-dioxane, b.p. 85°-91° C/0.025-0.03 mm Hg, nD25 1.5050. The ir and nmr spectra of the product were consistent with the assigned structure and showed the product to consist of 90% cis isomer.

Provenance & Evidence