Journal of the Chemical Society. Perkin transactions I p. 132 - 141 (1981)
Update date:2022-08-05
Topics:
Baylis, Christopher J.
Odle, Stanley W.
Tyman, John H. P.
Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-<(Z)-pentadec-8-enyl>resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-<(ZZ)-pentadeca-8,11-dienyl>resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'
View MoreJinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Contact:86-575-86132822，86-575-86085355
Address:No.418 Dadao West Road,Qixing Street,Xinchang, Zhejiang Province, China.
Zibo Kunran Enterprises Co. LTD
website:http://www.kunranchem.com
Contact:0086 533 5200669
Address:No. 96 Jinjing Avenue, Zibo, Shandong, China
NANCHANG QINZHI SCI&TEC.CO.,LTD(expird)
Contact:+86-13687004106
Address:Hero South Road,Hero Zone,Nanchang,Jiangxi,China
Contact:0510-85393305
Address:1619 Huishan Avenue, Huishan District, Wuxi,
Doi:10.1021/jo01027a004
(1964)Doi:10.1134/S1070363210040262
(2010)Doi:10.1055/s-1984-30887
(1984)Doi:10.1139/v62-215
(1962)Doi:10.1007/s10593-015-1724-3
(2015)Doi:10.1021/ja0019171
(2000)
