Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac
Keyword(s):
The presence of 3-(10′-phenyldecyl)-(2) (2%), 3-(12′-phenyldodecyl)- (3) (6%), 4-(10′-phenyldecyl)-(4) (0.3%) and 4-(12′-phenyldodecyl)- benzene-1,2-diol (5) (0.3%) in Burmese lac , the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristics of their bis-O-( trimethylsilyl ) derivatives with the derivatives of the natural products. Typically, 3,4- bis ( benzyloxy ) benzaldehyde (7) on Wittig reaction with triphenyl (11- phenylundecyl ) phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59% overall yield.
1973 ◽
Vol 28
(11-12)
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pp. 820-823
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2007 ◽
Vol 1166
(1-2)
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pp. 207-211
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1970 ◽
Vol 37
(2)
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pp. 285-292
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2011 ◽
Vol 1218
(39)
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pp. 7061-7064
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2010 ◽
Vol 20
(8)
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pp. 2500-2502
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1990 ◽
Vol 112
(1)
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pp. 83-87
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