Pentadecalactone → 15-Bromopentadecanoic acid

Participants

Reaction Steps

15-Pentadecanolide of 14.3 g (59.5 mmol), and 32% hydrogen bromide/acetic acid solution of 24.8 g (98.0 mmol, 1.6 eq) were added to 100 mL of autoclave protected with Teflon (registered trade name). After purging with nitrogen and sealing, the autoclave was placed in an oil bath at 60° C. and stirring was carried out for 16 hours. For the stirring, a magnetic stirrer was used. After cooling, 14 mL of water was added, and by using 200 mL of hot hexane the mixture was transferred to a separatory funnel. After washing with ion exchange water, it was dried over the magnesium sulfate. After filtration, 17.4 g of the target compound was obtained by crystallization using n-hexane (yield 91%).

Provenance & Evidence