Condensation product of oleyl alcohol with paraformaldehyde in acetic acid at the presence of sulfuric acid as the catalyst, were saponified and then fractionated by chromatography and recrystalization and the following substance was obtained.
The substance, mp 9394°C, seemed to have tetrahydropyranol-4 structure because of its characteristics (Fig.-3, Table-1) and it was considered as 3-heptyl-4-hydroxy-5-hydroxyoctyltetrahydropyrane (or 3-octyl-4-hydroxy-5-hydroxyheptyltetrahydropyrane).
As the catalyst, perchloric acid was most effective and sulfuric acid was also fairly effective (Fig. 1).