Butanedioic acid, [(4-hydroxy-3-methoxyphenyl)methylene]-, 1-methyl ester

Base Information

• Chemical Name: Butanedioic acid, [(4-hydroxy-3-methoxyphenyl)methylene]-, 1-methyl ester
• CAS No.: 111194-03-7
• Molecular Formula: C13H14O6
• Molecular Weight: 266.251
• Mol file: 111194-03-7.mol

Synonyms:

Chemical Property of Butanedioic acid, [(4-hydroxy-3-methoxyphenyl)methylene]-, 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Butanedioic acid, [(4-hydroxy-3-methoxyphenyl)methylene]-, 1-methyl ester

There total 1 articles about Butanedioic acid, [(4-hydroxy-3-methoxyphenyl)methylene]-, 1-methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

vanillin (121-33-5,8014-42-4) + Dimethyl succinate (106-65-0) → C13H14O6 (111194-03-7)

Guidance literature:

With lithium; In methanol; for 48h; Reflux;

DOI:10.1016/j.bmcl.2011.09.014

Reference yield: 70.0%

methanol (67-56-1) + C13H14O6 (111194-03-7) → C14H16O6 (190004-89-8)

Guidance literature:

With sulfuric acid; for 24h; Reflux;

DOI:10.1016/j.bmcl.2011.09.014

Reference yield:

C13H14O6 (111194-03-7) → 2,3-Bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol (3688-23-1,29388-59-8,57759-55-4,71772-17-3,75365-01-4,145265-02-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid / 24 h / Reflux

2: lithium / methanol / 48 h / Reflux

3: sulfuric acid / 24 h / Reflux

4: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 °C

With lithium aluminium tetrahydride; sulfuric acid; palladium 10% on activated carbon; hydrogen; lithium; In tetrahydrofuran; methanol; 2: Stobbe reaction;

DOI:10.1016/j.bmcl.2011.09.014

upstream raw materials:

vanillin

Dimethyl succinate

Downstream raw materials:

C₁₄H₁₆O₆

C₂₁H₂₀O₈

C₂₂H₂₂O₈

Refernces

• 1、 Mishra, Om P.,Simmons, Nicholas,Tyagi, Sonia,Pietrofesa, Ralph,Shuvaev, Vladimir V.,Valiulin, Roman A.,Heretsch, Philipp,Nicolaou,Christofidou-Solomidou, Melpo. "Synthesis and antioxidant evaluation of (S,S)- and (R,R)- secoisolariciresinol diglucosides (SDGs)". supporting information. p. 5325 - 5328. Retrieved 2013/09/23.