Megrin,Yoshitomi,Japan,1972
In 50 ml of pyridine were dissolved 50 grams of nicotinic acid and 50 grams
of p-toluene-sulfonyl chloride. While stirring, the mixture gradually became
hot and colorless, and finally solidified. To the mixture was added dropwise a
solution of 19 grams of 2-hexyl-2-(hydroxymethyl)-1,3-propanediol in 400 ml
of pyridine at a temperature below 80°C. The mixture was heated at 115° to
125°C on an oil bath for 1 hour. After cooling, the mixture was poured into
300 ml of ice water, and extracted with toluene. The toluene layer was washed
in sequence with water, aqueous sodium carbonate and water, dried over
potassium carbonate, and then the toluene was distilled off. The oily residue
was crystallized from ethanol to give 30 grams of 2-hexyl-2-(hydroxymethyl)-
1,3-propanediol trinicotinate, melting at 94° to 96°C. The yield was 59.5%.
