114802-12-9

Upstream product

• 13423-48-8 triphenylheptylphosphonium bromide 
• 114802-11-8 ethyl 6-(7-formylheptyl)-2-methoxybenzoate 
• 81036-11-5 7-(2-tetrahydro-2H-pyranyloxy)heptan-1-ol 
• 34335-17-6 7-(2-tetrahydropyranyloxy)heptanal 
• 629-30-1 1,7-heptandiol 
• 6555-40-4 ethyl 2-hydroxy-6-methylbenzoate 
• 332011-45-7 ethyl 6-(8-iodooctyl)-2-methoxybenzoate 
• 332011-43-5 ethyl 6-(8-chlorooctyl)salicylate 
• 332011-44-6 ethyl 6-(8-chlorooctyl)-2-methoxybenzoate 
• 332011-40-2 11-chloro-1,1-diethoxy-2-undecyne 
• 332011-42-4 11-chloro-3-methoxy-2-undecenal 
• 332011-41-3 11-chloro-2-undecynal 
• 28598-82-5 1-bromo-8-chloro-octane 
• 50816-19-8 8-bromooctanol 

Downstream Products

• 217449-17-7 ethyl 6-<8(Z)-pentadecenyl>salicylate 
• 22910-60-7 6-(8-pentadecenyl)salicylic acid 
• 114802-13-0 2-methoxy-6-(8-pentadecenyl)benzoic acid 

Relevant academic research and scientific papers

Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid

11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.

Synthesis of Saturated Anacardic Acids, and Alkenyl and Alkynyl Analogues

The C-alkylation of esters of 2-methoxy-6-methylbenzoic acid and of the 4-methyl isomers affords a route to homologous compounds including in the former case members of the natural anacardic acids from Anacardium occidentale and ω-alkynyl compounds suitable for synthesising other natural phenolic lipids or for structure/activity studies.

SYNTHESES OF ANACARDIC ACIDS AND GINKGOIC ACID

Syntheses of two anacardic acids , inhibitors of prostaglandin synthetase and of the growth of certain insects, and ginkgoic acid via directive metallation is reported.