An Efficient and Unambiguous Synthesis of 2-Hydroxymethyl-1, 3-Propanediol
- 1 January 1979
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 9 (5) , 431-435
- https://doi.org/10.1080/00397917908064173
Abstract
In 1949, Fujui3 reported the synthesis of what was presumed to be 2-hydroxymethyl-1, 3-propanediol (4) in 70% yield by the condensation of acetaldehyde with formaldehyde (1:2.5 molar ratio) in the presence of calcium hydroxide, and subsequent catalytic hydrogenation over a nickel catalyst. The product was reported to have a melting point of 182°. In 1955, the triester tris-(carbethoxy) methane (5) was reduced with lithium aluminum hydride to give a product with a reported melting point of 58–62°; the yield was only 5%.4 Owing to the conflicting data in the literature and the vast potential of 4; we have developed an efficient and unambiguous route to 4; this scheme is also adaptable to clean conversions to mono-, di- and tri-O-substituted derivatives of 4:Keywords
This publication has 4 references indexed in Scilit:
- Synthetic applications and mechanism studies of the decarbalkoxylations of geminal diesters and related systems effected in dimethyl sulfoxide by water and/or by water with added saltsThe Journal of Organic Chemistry, 1978
- Decarbalkoxylations of geminal diesters and β-keto esters in wet dimethyl sulfoxide. Effect of added sodium chloride on the decarbalkoxylation rates of mono- and di-substituted Malonate estersTetrahedron Letters, 1974
- Conformational analysis. XXIV. Effect of dipolar and eclipsing forces on intramolecular hydrogen bonding in 3-hydroxymethyltetrahydropyran and 5-hydroxymethyl-1,3-dioxaneJournal of the American Chemical Society, 1972
- Darstellung der di‐,tri‐ und tetra‐homologen Reihen der Methan‐methylol‐fettsäureester (XIV. Mitteil.1) über isomere und homologe Reihen)European Journal of Inorganic Chemistry, 1955