2,4-Hexadienoic acid, 3-methyl-6-oxo-, ethyl ester, (2E,4E)-

Base Information

• Chemical Name: 2,4-Hexadienoic acid, 3-methyl-6-oxo-, ethyl ester, (2E,4E)-
• CAS No.: 35482-69-0
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Mol file: 35482-69-0.mol

Synonyms:

Chemical Property of 2,4-Hexadienoic acid, 3-methyl-6-oxo-, ethyl ester, (2E,4E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,4-Hexadienoic acid, 3-methyl-6-oxo-, ethyl ester, (2E,4E)-

There total 1 articles about 2,4-Hexadienoic acid, 3-methyl-6-oxo-, ethyl 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: 56.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate → (E)-1,2-diphenyl-ethene (103-30-0) + ethyl (2E,4E)-3-methyl-6-oxo-2,4-hexadienoate (35482-69-0) + ethyl (2E,4E)-3-methyl-5-phenyl-2,4-pentanedienoate (41436-08-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 50 ℃; for 16h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.07.122

Reference yield:

ethyl (2E,4E)-3-methyl-6-oxo-2,4-hexadienoate (35482-69-0) → all-trans-13-demethyl-12-methylretinal (165604-88-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / NaBH₄ / ethanol; H₂O / 6.5 h / Ambient temperature

2: 100 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

3: 96 percent / DIBALH / tetrahydrofuran; hexane / 1 h / 0 °C

4: 81 percent / MnO₂ / diethyl ether / 2 h / Ambient temperature

5: 1.) n-BuLi / 1.) THF, hexane, a) -20 deg C, 30 min, b) -78 deg C, 30 min, 2.) THF, hexane, from -78 to -40 deg C, 7.5 h

6: (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature

7: 94 percent / MnO₂ / CH₂Cl₂ / 5 h / Ambient temperature

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00136a021

Reference yield:

ethyl (2E,4E)-3-methyl-6-oxo-2,4-hexadienoate (35482-69-0) → Butyl-[(2E,4E,6E,8E)-4,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(E)-ylidene]-amine

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / NaBH₄ / ethanol; H₂O / 6.5 h / Ambient temperature

2: 100 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

3: 96 percent / DIBALH / tetrahydrofuran; hexane / 1 h / 0 °C

4: 81 percent / MnO₂ / diethyl ether / 2 h / Ambient temperature

5: 1.) n-BuLi / 1.) THF, hexane, a) -20 deg C, 30 min, b) -78 deg C, 30 min, 2.) THF, hexane, from -78 to -40 deg C, 7.5 h

6: (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature

7: 94 percent / MnO₂ / CH₂Cl₂ / 5 h / Ambient temperature

8: molecular sieves 4A / diethyl ether / 0.5 h / Ambient temperature

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00136a021

upstream raw materials:

styrene

Downstream raw materials:

Ro 13-2389

ethyl (all-E)-retinoate

(2E,4E)-6-(3,5-Di-tert-butyl-phenylamino)-3-methyl-hexa-2,4-dienoic acid ethyl ester

(2E,4E)-6-[(3,5-Di-tert-butyl-phenyl)-methyl-amino]-3-methyl-hexa-2,4-dienoic acid ethyl ester

Refernces