40586-05-8

Upstream product

• 456-49-5 1-fluoro-3-methoxybenzene 
• 58932-93-7 acetaldehyde 7-chloroheptyl ethyl acetal 
• 40586-02-5 1-(3-methoxyphenyl)heptane-1,7-diol 
• 53821-21-9 6-(benzyloxy)-1-chlorohexane 
• 591-31-1 3-methoxy-benzaldehyde 
• 64-19-7 acetic acid 
• 59340-54-4 1-(2,3-dimethoxyphenyl)heptane-1,7-diol 
• 2009-83-8 6-chloro-1-hexanol 
• 2009-84-9 (chloro-6' hexyloxy)-2 tetrahydropyranne 
• 629-11-8 1,6-hexanediol 
• 629-30-1 1,7-heptandiol 
• 82393-86-0 1-(3-methoxyphenyl)-7-(2-tetrahydropyranyloxy)heptan-1-ol 
• 82393-85-9 acetaldehyde ethyl 7-hydroxy-7-(3-methoxyphenyl)heptyl acetal 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 40586-07-0 7-(3-methoxyphenyl)heptyl bromide 
• 51110-42-0 2-[10-(3-Methoxy-phenyl)-dec-2-ynyloxy]-tetrahydro-pyran 
• 51110-39-5 3-[10-(Tetrahydro-pyran-2-yloxy)-dec-8-ynyl]-phenol 
• 51110-45-3 3-(pentadeca-8,11-diynyl)anisole 
• 51110-43-1 10-(3-methoxyphenyl)dec-2-yn-1-ol 
• 51110-44-2 1-bromo-10-(3-methoxyphenyl)dec-2-yne 
• 51110-40-8 1-bromo-10-(3-hydroxyphenyl)dec-2-yne 
• 51110-38-4 10-(3-hydroxyphenyl)dec-2-yn-1-ol 
• 51110-46-4 3-<(Z,Z)-pentadeca-8,11-dienyl>anisole 
• 51110-41-9 3-(pentadeca-8,11-diynyl)phenol 
• 51546-63-5 3-[8(Z),11(Z)-pentadecadienyl] phenol 
• 40627-45-0 7-bromo-1-(3-hydroxyphenyl)heptane 

Relevant academic research and scientific papers

A synthesis of the phenolic lipid, 3-[(Z)-pentadec-8-enyl] catechol, (15:1)-urushiol

A synthesis of (15:1)-urushiol, urushiol monoene, 3-[(Z)-pentadec-8-enyl] catechol, 1,2-dihydroxy-3-[(Z)-pentadec-8-enyl] benzene, one of the toxic principles of Rhus toxicodendron and of Rhus vernicifera is described. 6-Chlorohexan-1-ol protected at the OH group with ethyl vinyl ether reacted with 2,3-dimethoxybenzaldehyde in the presence of lithium to give, after removal of the protective group with methanolic 4-toluenesulphonic acid, 1-(2,3-dimethoxyphenyl) heptane-1,7-diol. Catalytic hydrogenolysis in ethanol with palladium-carbon selectively afforded 7-(2,3-dimethoxyphenyl)heptane-1-ol accompanied by a small proportion of the 7-(3-methoxyphenyl)heptane-1-diol, formed by demethoxylation. Reaction of the dimethoxy compound with boron tribromide resulted in both bromination and demethylation to give 7-(2,3-dihydroxyphenyl) heptylbromide. This bromide in tetrahydrofuran (THF) containing hexamethylphosphoric triamide reacted with excess lithium oct-1-yne to give 3-(pentadec-8-enyl)catechol which, by catalytic hydrogenation in ethyl acetate containing quinoline, selectively formed the required cis product, 3-[(Z)-pentadec-8-enyl]catechol which was identical chromatographically and spectroscopically with urushiol monoene separated from the natural product.