Description
11-Bromoundecanoic acid is a bromo-modified undecanoic acid derivative. 11-Bromoundecanoic acid was used in the synthesis of 11-phenoxyundecyl phosphate and 11-hydroxytetradecanoic acid. It has been used as a reactant for the preparation of hydroxy-substituted naphthoquinone cations as antiplasmodial agents.
References
Navarro, I, G. Fabriás, and F. Camps. "Synthesis of [14, 14, 14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis." Bioorganic & Medicinal Chemistry 4.3(1996):439-443.
https://www.trc-canada.com/product-detail/?B688880
http://www.sigmaaldrich.com/catalog/product/aldrich/165816?lang=en®ion=US
Chemical Properties
faintly beige crystalline solid
Uses
11-Bromoundecanoic acid was used in the synthesis of 11-phenoxyundecyl phosphate and 11-hydroxytetradecanoic acid.
Definition
ChEBI: 11-bromo-undecanoic acid is a medium-chain fatty acid.
General Description
11-Bromoundecanoic acid reacts with potassium salt of dimethyl hydantoin to yield 4,4-dimethyl hydantoin-undecanoic acid.
Synthesis
1 kg of 10-undecylenic acid having a melting point of 23° C. and a purity of more than 98.5% was used as the raw material, and it was mixed according to the ratio of the mass ratio of 10-undecylenic acid to toluene of 1:3. According to the ratio of the molar ratio of 10-undecylenic acid to hydrogen bromide of 1:1.20, hydrogen bromide gas was continuously passed through from the bottom of the charging tower, while feed liquid was continuously added to maintain the ratio. The reactor temperature was controlled at 18°C by cooling water and the reaction lasted for 1 hour. Upon completion of the reaction, toluene was recovered by distillation. The oil phase is washed 2-3 times and the system is cooled to 1520°C to promote crystallization. After complete crystallization, vacuum filtration was performed to obtain 1.34 kg of white crystals 11-bromoundecanoic acid.
References
[1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193
[2] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4785 - 4786
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1183 - 1190
[4] Bulletin of the Chemical Society of Japan, 1938, vol. 13, p. 334
[5] Journal of the Chemical Society, 1934, p. 439
