Abstract
Dodecanal was reacted with formaldehyde and potassium hydroxide in ethanol and with formaldehyde and calcium oxide in aqueous methanol to give about 30% of the theoretical yield of 2-decyl-2-hydroxymethyl-1, 3-propanediol (DHP).
Petroselinic acid was ozonized in methylene chloride, and the ozonide reduced to aldehydes with formic acid and zine. The methylene chloride solution was emulsified with water and reacted with formaldehyde and potassium hydroxide. A yield of 32% of DHP was isolated.
Pure 5,5,5-trimethylol valeric acid could not be isolated from the reaction mixture of formaldehyde and potassium hydroxide with the mixed aldehydes from petroselinic acid, but a small amount of material was isolated by ion exchange resins which had high infrared absorption for hydroxyl and carboxylic acid and which polymerized on standing.
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A laboratory of the So. Utiliz. Res. Dev. Div., ARS, USDA.
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Holmes, R.L., Moreau, J.P. Preparation of 2-decyl-2-hydroxymethyl-1, 3-propanediol from dodecanal and from petroselinic acid. J Am Oil Chem Soc 42, 833–835 (1965). https://doi.org/10.1007/BF02541169
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DOI: https://doi.org/10.1007/BF02541169