95690-68-9Relevant academic research and scientific papers
Synthesis of 3- and 4-(ω-Phenylalkyl)catechols, the Sap Exuded from a Burmese Lac Tree, Melanorrhoea Usitate
Miyakoshi, Tetsuo,Du, Yumin,Kumanotani, Ju
, p. 1054 - 1056 (2007/10/02)
The presence of 3- and 4-(ω-phenylalkyl)catechols in Burmese lac has been confirmed by their synthesis. 3-(ω-Phenylalkyl)veratroles were synthesized by alkylation of ω-phenylalkyl bromide with aryl lithium derived from veratrole. 4-(ω-phenylalkyl)veratroles were similarly obtained from w-phenylalkyl bromide and 4-bromoveratrole.Demethylation of 3- and 4-(ω-phenylalkyl)veratroles with boron tribromide gave the corresponding catechols in good yields.
Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac
Jefferson, Alan,Sargent, Melvyn V.,Wangchareontrakul, Sirichai
, p. 19 - 25 (2007/10/02)
The presence of 3-(10'-phenyldecyl)- (2) (2percent), 3-(12'-phenyldodecyl)- (3) (6percent), 4-(10'-phenyldecyl)- (4) (0.3percent) and 4-(12'-phenyldodecyl)-benzene-1,2-diol (5) (0.3percent) 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 characteristic 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 59percent overall yield.
