Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

Base Information

• Chemical Name: Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate
• CAS No.: 69427-41-4
• Molecular Formula: C23H30O3
• Molecular Weight: 354.489
• European Community (EC) Number: 831-628-0
• DSSTox Substance ID: DTXSID60860667
• Mol file: 69427-41-4.mol

Synonyms:13-cis-Etretinate;Ro 13-7837;Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate;69427-41-4;2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, ethyl ester, (Z,E,E,E)-;DTXSID60860667;LS-96926

Chemical Property of Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

Chemical Property:

• Vapor Pressure: 2.22E-10mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Boiling Point: 506.4°Cat760mmHg
• Flash Point: 219.4°C
• PSA: 35.53000
• Density: 1.006g/cm³
• LogP: 5.64550
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 354.21949481
• Heavy Atom Count: 26
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C(=C(C=C1C)OC)C)C
• Isomeric SMILES: CCOC(=O)/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C(=C(C=C1C)OC)C)C

Technology Process of Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

There total 7 articles about Ethyl (13-cis)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-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: 9.0%

Ethyl-4-hydroxy-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,5,7-trienoat (124743-96-0) → etretinate (54350-48-0) + ethyl (2E,4E,6Z,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-40-3) + ethyl (2Z,4E,6E,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-41-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/hlca.19890720224

Reference yield:

ethyl (E)-3-formyl-2-butenoate (62054-49-3) → ethyl (2Z,4E,6E,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-41-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1.5 M BuLi / 1.) THF/hexane, -30 deg C, 2.) THF/hexane, 2 h, room temperature

2: 97 percent / hydrogen / Lindlar-catalyst, 1,2-bis<(2-hydroxyethyl)thio>ethane / ethanol / 4 h / Ambient temperature

3: 13 percent / TsOH*H₂O / CH₂Cl₂ / 2 h / Ambient temperature

With n-butyllithium; hydrogen; toluene-4-sulfonic acid; Lindlar's catalyst; 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol; In ethanol; dichloromethane;

DOI:10.1002/hlca.19890720224

Reference yield:

3-methyl-1-penten-4-yn-3-ol (3230-69-1) → ethyl (2Z,4E,6E,8E)-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (69427-41-4)

Guidance literature:

Multi-step reaction with 4 steps

1: MgSO₄, BF₃*Et₂O / 1 h / 5 °C

2: 1.) 1.5 M BuLi / 1.) THF/hexane, -30 deg C, 2.) THF/hexane, 2 h, room temperature

3: 97 percent / hydrogen / Lindlar-catalyst, 1,2-bis<(2-hydroxyethyl)thio>ethane / ethanol / 4 h / Ambient temperature

4: 13 percent / TsOH*H₂O / CH₂Cl₂ / 2 h / Ambient temperature

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; magnesium sulfate; toluene-4-sulfonic acid; Lindlar's catalyst; 2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol; In ethanol; dichloromethane;

DOI:10.1002/hlca.19890720224

upstream raw materials:

Ethyl-4-hydroxy-9-(4-methyoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,5,7-trienoat

ethyl (E)-3-formyl-2-butenoate

3-methyl-1-penten-4-yn-3-ol

2,3,5-trimethylanisole

Refernces