Total synthesis of linoleic acid was written by Baudart, Pierre. And the article was included in Bulletin de la Societe Chimique de France in 1944.Recommanded Product: 1-Bromo-6-methoxyhexane This article mentions the following:
A linoleic acid was synthesized and shown to be a stereoisomer of the natural acid. Intermediates prepared include 1-methoxypentane, b760 100-2°; 1-bromopentane, b760 122-4°, nD25 1.4290, d425 1.1552; 1,6-hexanediol, b3 121-4°; 1,6-dibromohexane, b3 77-80°; 1-bromo-6-methoxyhexane, nD25 1.4469, d425 1.1887. Glutardialdoxime (cf. Shaw, C.A. 31, 3008.1) (180 g.) and 240 g. EtONO were added gradually in alternate portions to 50 mL. 95% EtOH containing 5 mL. AcOH at 0°. The mixture was acidified with EtOH-HCl and allowed to stand 5 h. at 0° and 48 h. at room temperature over CaCl2, yielding after ether extraction and distillation 175 g. glutaraldehyde bis(di-Et acetal) (I), b3 97-100°, nD25 1.4232; d25 0.9009. I was reacted with 290 g. PCl5.EtCl at 30-40°, the POCl3 removed under vacuum, and the residue of 1,5-diethoxy-1,5-dichloropentane (II) distilled, b0.8 90-100° (partial decomposition); yield 118 g. II with Br at 0° gave 240 g. impure, very unstable 1,5-diethoxy-1, 2, 4, 5-tetrabromopentane (III), which was used at once. To III in Et2O at 0° were added Et2O solutions of 78 g. AmMgBr and 120 g. MeO(CH2)6Br (cf. Dionneau, C.A. 1, 2683). The product was isolated and reduced with powd. Zn in BuOH (cf. Boord, et al., C.A. 27, 4770), yielding after distillation 11 g. impure 1-methoxy-7,10-hexadecadiene (IV), b3 144-7, as well as 6, 9-pentadecadiene and 1, 17-dimethoxy-7, 10-heptadecadiene. IV (9 g.) was reacted with Br at 0°, then with HBr at 100-130°, and finally debrominated with Zn in EtOH to produce 8 g. 1-bromo-7, 10-hexadecadiene (V), b0.3 136-40°. V was transformed to the iodide with NaI in acetone, reacted with NaCH(CO2Et)2, decarboxylated, and distilled, giving 3.2 g. of a linoleic acid, b0.8 179-83°; iodine number 152. Bromination of 2 g. of acid produced a large amount of an oily bromide and 0.35 g. of a tetrabromide, m. 77-8°, identical with the bromide of natural linoleic acid elaidinized by Se (cf. Kass and Burr, C.A. 33, 6239.8). In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Recommanded Product: 1-Bromo-6-methoxyhexane).
1-Bromo-6-methoxyhexane (cas: 50592-87-5) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Recommanded Product: 1-Bromo-6-methoxyhexane
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary