Synthesis of some derivatives of juniperic acid was written by Plesek, Jaromir. And the article was included in Chemicke Listy pro Vedu a Prumysl in 1956.HPLC of Formula: 56523-59-2 This article mentions the following:
ω-Bromopalmitic acid (I), obtained in a 3-g. yield by saturating an Et2O solution of 3 g. 1-pentadecene-15-carboxylic acid with HBr in the presence of 0.02 g. Bz2O2. crystals from ligroine, m. 70-1°. A solution of 2.5 g. I in 100 mL. MeCOEt (II) was dropped during 30 h. into 1000 mL. boiling II containing 20 g. dry K2CO3 and the mixture refluxed 8 h. After evaporating II, the residue was dissolved in 30 mL. ligroine, the insoluble K salts and a dilactone were filtered off and the filtrate was distilled, yielding 1.5 g. crystalline 1,16-hexadecanolide (III), b0.5 124°, m. 18°, besides 10 g. of a forerun, b0.5 100°, consisting of a condensation product of II. Saponification of III by boiling 40% aqueous NaOH gave juniperic acid, m. 94-5° (from C6H6) in a 98% yield. 1-Bromopentadecan-11-one-15-carboxylic acid (IV) was prepared by the Grignard reaction from 21 g. Et cyclopentanonecarboxylate and 26.5 g. ω-bromoundecyl chloride. The reaction product was boiled with AcOH and aqueous HBr and poured into water, yielding 20 g. IV, m. 77-8° (from C6H6-ligroine), obtained more easily in an 80%-yield by addition of HBr to 1-pentadecen-11-one-15-carboxylic acid in the presence of Bz2O2. A solution of 13.5 g. IV in 570 mL. II was dropped during 48 h. into a boiling suspension of dry K2CO3 in 3000 mL. II and refluxed 16 h., yielding 9 g. 6-oxo-1,16-hexadecanolide (V), b0.5 155°, m. 35°. Saponification of V by boiling with alc. KOH gave a 98% yield 6-oxojuniperic acid, m. 94-5° (from C6H6); semicarbazone, m. 147-8° (from EtOH). In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2HPLC of Formula: 56523-59-2).
15-Bromopentadecanoic acid (cas: 56523-59-2) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbonbromine bond is electrophilic in nature. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.HPLC of Formula: 56523-59-2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary