Synthesis of 6-(10-hydroxy-[1-14C]decyl) -2,3-dimethoxy-5-methyl-1,4-benzoquinone

✍ Scribed by Nobuyoshi Hayashi; Shinji Kato

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: French
• Weight: 275 KB
• Volume: 22
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580221009

✦ Synopsis

Jusohonmachi 2-chomer Yodogawa-ku, Osaka? Japan SUMMARY 6-( 10-Hydroxy-[l-14Cldecyl) -2,3-dimethoxy-5-methyl-1,4-benzoquinone (VIII) having a specific activity of 23.4 mCi/mmol was synthesized. 9-(2-Hydroxy-3,4-dimethoxy-6methyl-[ carbonyl-4C]benzoyl) nonanol (VI) was obtained from the condensation of 3,4,5-trimethoxytoluene with 10-a~etoxy-[l-~~C]decanoyl chloride (V) prepared from K14CN (I). Reduction of VI with hydrogen in the presence of Pd-C provided 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl) -[1-14C]decanol (VII). VII was oxidized with a Fremy's salt to give VIII in 21.5% radiochemical yield. 6-(lO-Hydroxy-14 decyl)-2-methoxy-3-[ C]methoxy-5-methyl-l,4-benzoquinone (XI) was prepared in 34.6% radiochemical yield from the reaction of [ Cldimethyl sulfate with 6-(10-hydroxydecyl)-3-hydroxy-2-methoxy-5-methyl-l,4-benzoquinone.