Journal of the Chemical Society. Perkin transactions I p. 1942 - 1952 (1981)
Update date:2022-08-04
Topics:
Kiong, Lam Soot
Tyman, John H. P.
(15:0)-Anacardic acid (6-pentadecylsalicylic acid), prepared by reduction of unsaturated anacardic acid from Anacardium occidentale, has been converted into anacardic alcohol (6-pentadecylsalicylic alcohol) and thence by oxidation at carbon into anacardaldehyde.Phenolic oxidation of anacardic alcohol led to 8-pentadecyl-1-oxaspiro<2.5>octa-5,7-dien-4-one, itself readily convertible photochemically, but less so thermally, into anacardaldehyde.Reaction of thionyl chloride with anacardic acid led mainly to the anhydride, which by hydride reduction gave anacardaldehyde less satisfactorily.Dakin oxidation of anacardaldehyde furnished (15:0)-urushiol (3-pentadecylcatechol) identical chemically and from argentation t.l.c. with the hydrogenated natural product from Rhus vernicifera. (15:0)-Cardanol (3-pentadecylphenol) has been detected in hydrogenated urushiol.The composition of the unsaturated constituents of urushiol from Rhus vernicifera and Rhus toxicodendron and its mode of formation have been discussed.An improved synthesis of (15:0)-urushiol has been devised based on an organo-lithium route.Aromatic methyl ether and ester formation in this series is greatly facilitated by phase-transfer catalysis.
View MoreSuzhou SuKaiLu Chemical Technology Co., Ltd.
Contact:+86-512-62766020
Address:Floor 4, Building 1, Xinyi Pharmaceutical Valley Wisdom Industrial Park, 415 Changyang Street, Suzhou Industrial Park, Jiangsu Province
Suqian Ruixing Chemical Co., Ltd.
Contact:+86-527-80805666（总机）;84836008(销售)
Address:3 Jingsilu, Zone north, Hubin Xincheng Development Park, Suqian, China
Guangzhou PI & PI Biotech Inc. Ltd.
Contact:+86-20-81716320
Address:13th Floor, Xinbao Technology Industrial Park, No. 2 Ruixiang Road, Huangpu District, Guangzhou,Guangdong,China
Beijing Harmony Chemical Co., Ltd.
Contact:86-010-84956928
Address:Room 207, Jin feng he B building, No 8 Xin Jie Kou Wai Street, Xi Cheng District, Beijing,PRC. 10008
Chengdu Pukang Biotechnology Co., Ltd
Contact:+86-28-82550498
Address:No. 558 Rulin Road,Xinjin county,Chengdu city, China
Doi:10.1139/v81-311
(1981)Doi:10.1039/P19810002680
(1981)Doi:10.1021/ja01292a047
(1936)Doi:10.3390/molecules24162950
(2019)Doi:10.1021/acs.orglett.7b00386
(2017)Doi:10.1021/jf062819n
(2007)
