A ONE-POT SYNTHESIS OF COUMARYL, CONIFERYL AND SINAPYL ALCOHOL

被引:11
作者
ROTHEN, L [1 ]
SCHLOSSER, M [1 ]
机构
[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND
关键词
D O I
10.1016/S0040-4039(00)74358-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The side chain of 4-allylphenol can be easily deprotonated if the butyllithium/potassium tert-butoxide superbase is employed. Consecutive treatment with fluorodimethoxyboron and hydrogen peroxide affords directly 3-(4-hydroxy-phenyl)-2-propen-1-ol (''coumaryl alcohol''). In the same way, 4-allyl-2-methoxyphenol can be converted to coniferyl alcohol and 4-allyl-2,6-dimethoxyphenol to sinapyl alcohol.
引用
收藏
页码:2475 / 2476
页数:2
相关论文
共 14 条
[1]   NEW SYNTHESIS OF PHENOLIC LIGNIN PRECURSORS USING IMINIUM SALTS OF PARA-HYDROXY CINNAMIC-ACIDS [J].
DURAN, E ;
GORRICHON, L ;
CAZAUX, L ;
TISNES, P .
TETRAHEDRON LETTERS, 1984, 25 (26) :2755-2758
[2]   *CONIFERYLALKOHOL AUS SIAMBENZOE [J].
FREUDENBERG, K ;
BITTNER, F .
CHEMISCHE BERICHTE-RECUEIL, 1950, 83 (06) :600-604
[3]   CONIFERYLALDEHYD UND SINAPINALKOHOL [J].
FREUDENBERG, K ;
DILLENBURG, R .
CHEMISCHE BERICHTE-RECUEIL, 1951, 84 (01) :67-70
[4]   CONTRIBUTIONS TO LIGNIN RESEARCH [J].
FREUDENBERG, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1956, 68 (16) :508-512
[5]   SYNTHESIS OF CONIFERYL AND DIHYDROCONIFERYL DERIVATIVES USING RADICAL BROMINATION WITH N-BROMOSUCCINIMIDE AS THE KEY STEP [J].
LINDEBERG, O .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1980, 34 (01) :15-20
[6]  
PAULY H, 1923, CHEM BER, V56, P609
[7]   SYNTHESIS OF SOME DE AND CDE RING ANALOGS OF CAMPTOTHECIN [J].
PLATTNER, JJ ;
GLESS, RD ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (24) :8613-&
[8]   SELECTIVE SYNTHESIS WITH ORGANOMETALS .4. DIRECT HYDROXYLATION OF ALLYL POSITIONS [J].
RAUCHSCHWALBE, G ;
SCHLOSSER, M .
HELVETICA CHIMICA ACTA, 1975, 58 (04) :1094-1099
[9]  
Sarkanen, 1971, LIGNINS
[10]   SUPERBASES FOR ORGANIC-SYNTHESIS [J].
SCHLOSSER, M .
PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1627-1634