ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate

Base Information

• Chemical Name: ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate
• CAS No.: 168416-28-2
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 332.46
• Mol file: 168416-28-2.mol

Synonyms:ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate

Chemical Property of ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate

There total 7 articles about ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate 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:

ethyl 3-methylbut-2-enoate (638-10-8) → ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate (168416-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C

2: 98 percent / DIBAL / tetrahydrofuran / 0.25 h / -78 °C

3: 86 percent / aq. HCl / 1,2-dichloro-ethane / 1 h / 55 °C

4: 1.) n-BuLi, DMPU / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, -78 deg C, 60 min

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1002/jlcr.2580360807

Reference yield:

<(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone (168416-22-6) → ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate (168416-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. HCl / ethanol / 4 h / 82 °C

2: 1.) n-BuLi, TMEDA / 1.) hexane, a) -78 deg C, 30 min, b) RT, 4 h, 2.) hexane, RT, 12 h

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C

4: 98 percent / DIBAL / tetrahydrofuran / 0.25 h / -78 °C

5: 86 percent / aq. HCl / 1,2-dichloro-ethane / 1 h / 55 °C

6: 1.) n-BuLi, DMPU / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, -78 deg C, 60 min

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane;

DOI:10.1002/jlcr.2580360807

Reference yield:

<(R,S)-6-<13CD3>>-2,6,6-trimethyl-1-cyclohexene-1-aldehyde (168416-24-8) → ethyl (R,S)-(2E,4E,6Z,8E)-3,7-dimethyl-9-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)nonatetraenoate (168416-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C

2: 98 percent / DIBAL / tetrahydrofuran / 0.25 h / -78 °C

3: 86 percent / aq. HCl / 1,2-dichloro-ethane / 1 h / 55 °C

4: 1.) n-BuLi, DMPU / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, -78 deg C, 60 min

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1002/jlcr.2580360807

upstream raw materials:

diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate

(R,S)-(2Z,4E)-3-methyl-5-(6-<13CD3>-2,6,6-trimethylcyclohex-1-en-1-yl)-2,4-pentadienenal

ethyl 3-methylbut-2-enoate

<(R,S)-2-<13CD3>>-2,2,6-trimethylcyclohexanone