2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)-

Base Information

• Chemical Name: 2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)-
• CAS No.: 692-91-1
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.165
• DSSTox Substance ID: DTXSID10988906
• Mol file: 692-91-1.mol

Synonyms:dimethyl hexa-2,4-dienedioate;2,4-Hexadienedioic acid, dimethyl ester, (E,Z)-;NCIOpen2_001759;dimethyl hex-2,4-diendioate;DTXSID10988906;PXYBXMZVYNWQAM-UHFFFAOYSA-N;hexa-2,4-dienedioic acid dimethyl ester

Chemical Property of 2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)-

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C=CC=CC(=O)OC

Technology Process of 2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)-

There total 2 articles about 2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)- 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: 3.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + acetylene (74-86-2,25067-58-7) → cis,cis-dimethyl muconate (692-91-1,692-92-2,1119-43-3,1733-37-5) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + dimethylfumarate (624-49-7)

Guidance literature:

PdI₂-KI; at 60 ℃; for 15h; under 19000 Torr;

Reference yield:

methyl (2Z)-3-iodoprop-2-enoate (6214-23-9) + ((E)-2-iodovinyl)cyclohexane (42599-23-5) → cis,cis-dimethyl muconate (692-91-1,692-92-2,1119-43-3,1733-37-5) + (2Z,4E)-hexa-2,4-dienedioic acid dimethyl ester (692-92-2) + (E,E)-hexa-2,4-dienedioic acid dimethyl ester (1119-43-3) + (2E,4E)-methyl 5-cyclohexylpenta-2,4-dienoate (77811-12-2)

Guidance literature:

With silver(I) acetate; palladium diacetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In acetonitrile; at 50 ℃; for 20h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/adsc.200700464

Reference yield: 100.0%

cis,cis-dimethyl muconate (692-91-1,692-92-2,1119-43-3,1733-37-5) + Dimethylphenylsilane (766-77-8) → 6-methoxy-6-(dimethylphenylsiloxy)-(3E,5Z)-hexadienoate (132664-29-0)

Guidance literature:

With RhCl(PPh₃)3; In benzene; for 10h; Heating;

DOI:10.1016/0022-328X(92)83240-I

upstream raw materials:

methanol

carbon monoxide

acetylene

methyl (2Z)-3-iodoprop-2-enoate

Downstream raw materials:

cis,cis-Muconic acid

Methyl-N-cyclohexyl-4-keto-adipamat

N,N'-Dicyclohexyl-3-keto-adipamid

3,4-Dibenzylaminoadipinsaeuredimethylester

Refernces

• 1、 Gabriele, Bartolo,Costa, Mirco,Salerno, Giuseppe,Chiusoli, Gian Paolo. "An Efficient and Selective Pallladium-catalysed Oxidative Dicarbonylation of Akynes to Alkyl- or Aryl-maleic Esters". . p. 83 - 88. Retrieved 2007/10/02.