2,6-Octadienoic acid, 8-hydroxy-2,6-dimethyl-, methyl ester, (2E,6E)-

Base Information

• Chemical Name: 2,6-Octadienoic acid, 8-hydroxy-2,6-dimethyl-, methyl ester, (2E,6E)-
• CAS No.: 40772-83-6
• Molecular Formula: C₁₁H₁₈O₃
• Molecular Weight: 198.262
• Mol file: 40772-83-6.mol

Synonyms:

Chemical Property of 2,6-Octadienoic acid, 8-hydroxy-2,6-dimethyl-, methyl ester, (2E,6E)-

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,6-Octadienoic acid, 8-hydroxy-2,6-dimethyl-, methyl ester, (2E,6E)-

There total 1 articles about 2,6-Octadienoic acid, 8-hydroxy-2,6-dimethyl-, methyl ester, (2E,6E)- 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:

methanol (67-56-1) + 2'-O,8-O-difoliamenthoyleuphroside → 2,6-trans-2,6-dimethyl-8-hydroxy-2,6-octadienoic acid methyl ester (40772-83-6) + 8-O-foliamenthoyleuphroside

Guidance literature:

With sodium methylate; for 1h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0031-9422(00)84509-4

Reference yield:

2,6-trans-2,6-dimethyl-8-hydroxy-2,6-octadienoic acid methyl ester (40772-83-6) → methyl 1-p-menthen-9-oate

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / CBr₄; triphenylphosphine / benzene / 2 h / 0 °C

2.1: tributyltin hydride; AIBN / benzene / 80 °C

2.2: 72 percent / aq. KF / benzene / 2 h / 20 °C

With 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tri-n-butyl-tin hydride; triphenylphosphine; In benzene;

DOI:10.1021/jo062630a

Reference yield:

2,6-trans-2,6-dimethyl-8-hydroxy-2,6-octadienoic acid methyl ester (40772-83-6) → [5-((2E,6E)-8-Hydroxy-3,7-dimethyl-octa-2,6-dienyl)-2,6,6-trimethyl-cyclohex-1-enyl]-acetonitrile (67517-33-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / triphenylphosphine, CCl₄ / 1 h / Heating

2: 34 percent / SnCl₄ / CH₂Cl₂ / 3 h / -90 - -30 °C

3: 96 percent / LiCl / dimethylformamide / 3 h / 100 °C

4: 87 percent / AlH₃, ZnCl₂ / diethyl ether / 3 h / -78 °C

With aluminium hydride; tetrachloromethane; tin(IV) chloride; triphenylphosphine; lithium chloride; zinc(II) chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.69.221

upstream raw materials:

methanol

Downstream raw materials:

((2E,6E)-7-Methoxycarbonyl-3-methyl-octa-2,6-dienyl)-triphenyl-phosphonium; bromide

[5-((2E,6E)-8-Hydroxy-3,7-dimethyl-octa-2,6-dienyl)-2,6,6-trimethyl-cyclohex-1-enyl]-acetonitrile

(2E,6E)-8-(3-Cyanomethyl-2,2,4-trimethyl-cyclohex-3-enyl)-2,6-dimethyl-octa-2,6-dienoic acid methyl ester

[5-((2E,6E)-8-Chloro-3,7-dimethyl-octa-2,6-dienyl)-2,6,6-trimethyl-cyclohex-1-enyl]-acetonitrile

Refernces