dc.contributor.advisor | Stenstrøm, Yngve H. | |
dc.contributor.advisor | Ekeberg, Dag | |
dc.contributor.advisor | Devle, Hanne | |
dc.contributor.advisor | Aarum, Ida Synnøve | |
dc.contributor.author | Løken, Morten Hvattum | |
dc.date.accessioned | 2018-11-26T13:16:23Z | |
dc.date.available | 2018-11-26T13:16:23Z | |
dc.date.issued | 2018 | |
dc.identifier.uri | http://hdl.handle.net/11250/2574885 | |
dc.description.abstract | Målet med oppgaven var å syntetisere trimeren 5-((3-hydroksy-1-(4-hydroksy-3,5-dimetoksyfenyl)-2-(2-metoksyfenoksy)propoksy)metyl)furan-2-karbaldehyd (14). Denne trimeren er et mulig biprodukt av dampeksplosjon hvor ett dehydrert karbohydrat har reagert med lignin. Syntesen ble delt opp i to seksjoner. Det første steget var å syntetisere aryleteren, 3-hydroksy-1-(4-hydroksy-3,5-dimetoksyfenyl)-2-(2-metoksyfenoksy)propan-1-on (11).
Syntesen av aryleteren 11 er basert på det kommersielt tilgjengelige alfaketonet, 3,5-dimetoksy-4-hydroksyacetofenon (4) som startmateriale. Dette ble gjort via en beskyttelsesreaksjon, halogenering og Williamson eterkobling.
Det ble dokumentert spektraldata for tre nye forbindelser (8, 9 og 10) som ikke var kjent fra litteraturen.
For å fullføre det første steget av syntesen ble det forsøkt to ulike aldolreaksjoner, det ble forsøkt en hydroksymetylering med vandig formaldehyd (37 % løsning) og en med paraformaldehyd. Paraformaldehyd reaksjonen ble utført bare en gang.
Videre undersøkelse av paraformaldehydreaksjonen vil trolig føre til syntese av forbindelse 11. | nb_NO |
dc.description.abstract | Synthetic studies towards the hetero-trimer 5-((3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propoxy)methyl)furan-2-carbaldehyde (14). This hetero-trimer is a possible biproduct from steam explosion, where a dehydrated carbohydrate reacts with lignin. The synthesis was split into two sections. The first step was synthesis the aryl ether 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propan-1-one (11).
The synthesis of compound 11 is based on the commercially available alpha-ketone 3,5 dimethoxy-4-hyroxyacetophenone (4). From this start material, the protected phenone (8) was produced. Compound 8 was halogenated (9) and combined with 2-methoxyfenol to produce compound 10.
Spectral data for compound 8, 9 and 10 was documented, since there were no records of their data in the literature.
To complete the synthesis of compound 11, two aldol reactions were tested. Combining a hydroxymethyl group to compound 10, with aqueous formalin (37 % wt) and paraformaldehyde. The paraformaldehyde reaction was only tested once.
Further examination of the paraformaldehyde reaction could lead to the synthesis of compound 11. | nb_NO |
dc.language.iso | nob | nb_NO |
dc.publisher | Norwegian University of Life Sciences, Ås | nb_NO |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internasjonal | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/deed.no | * |
dc.title | Syntese av 5-((3-hydroksy-1-(4-hydroksy-3,5-dimetoksyfenyl)-2-(2-metoksyfenoksy)propoksy)metyl)furan-2-karbaldehyd og undersøkelse av mulige endringer av lignin etter dampeksplosjon | nb_NO |
dc.title.alternative | Synthesis of lignin substructure 5-((3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propoxy)methyl)furan-2-carbaldehyde and it’s change after steam explosion | nb_NO |
dc.type | Master thesis | nb_NO |
dc.description.localcode | M-KJEMI | nb_NO |