Sulfuric Acid → HCID 178443321, compound

Participants

Reaction Steps

A solution of 2.2 g of 6-[4-(octyloxy)phenyl]-3-pyridinecarboxaldehyde (prepared in accordance with Example 2) and 1.4 g of 2-decyl-1,3-propanediol in 40 ml of toluene was treated with 5 drops of 10 percent (v/v) sulfuric acid. The mixture was heated to boiling for 1 hour, moist toluene being distilled off and being replaced by fresh toluene. The reaction mixture was then neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 9:1) and repeated recrystallization of the trans/cis mixture from ethyl acetate gave 0.56 g of pure 5-(trans-5-decyl-1,3-dioxan-2-yl)-2-[4-(octyloxy)phenyl]pyridine; m.p. (C-S) 69.7° C., transition S-SC 137.5° C., cl.p. (SC -I) 179° C.

Provenance & Evidence