US EPA

7501772 

Journal Article 

Synthese von guajacylglycerin-β-guajacyläther 

Nakatsubo, F; Sato, K; Higuchi, T 

1975 

1 

Holzforschung
ISSN: 0018-3830
EISSN: 1437-434X 

29 

5 

165-168 

English 

10.1515/hfsg.1975.29.5.165 

Guaiacylglycerol-β-guaiacyl ether (1), the model compound of arylglycerol-β-aryl ether structure in lignin was synthesized in high yield through five reaction steps from vanillin. The key step of this synthetic method was the condensation reaction between ethyl 2-methoxyphenoxy acetate (4) and benzyl vanillin (5). At this step, lithium diisopropyl amide was used as the basea and β-hydroxy ester (6) was obtained in 95 % yield as an oily substance consisted of two isomers, from which only erythro isomer was obtained as crystal in 51 % yield. The residual oily substance was converted to its carbamate (7) and crystallized in 70% yield. The crystalline β-hydroxy ester (6) and the carbamate (7) were then converted to the final compound (1) by the lithium aluminum hydride reduction and subsequent hydrogenation with Pd-C. The overall yield of the guaiacylglycerol-β- guaiacyl ether (1) from benzyl vanillin (5) was about 72%. © 1975, Walter de Gruyter. All rights reserved. 

Carbamat; Carbamate; Convergent synthesis; Erythro and threo isomers; Erythro und threo Isomere; Ethyl 2-methoxyphenoxy acetate; Guaiacylglycerol-β-guaiacyl ether; Guajacylglycerin-β-guajacyläther; Konvergente Synthese; Lithium diisopropyl amide; Lithium diisopropylamid; Äthyl-2-methoxyphenoxyacetat