(2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal

Base Information

• Chemical Name: (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal
• CAS No.: 122203-78-5
• Molecular Formula: C₂₂H₂₈O₂
• Molecular Weight: 324.463
• Mol file: 122203-78-5.mol

Synonyms:

Chemical Property of (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal

There total 10 articles about (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal 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:

methyl (E)-3-formylcrotonate (40835-18-5) → (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal (122203-78-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

2: 9 g / lithium aliminium hydrid / diethyl ether / 0.5 h / 0 °C

3: MnO₂ / CH₂Cl₂ / 20 h / Ambient temperature

4: 95 percent / n-BuLi / hexane; diethyl ether / 1.5 h / Ambient temperature

5: 7.15 g / lithium aluminium hydrid / diethyl ether / 0.5 h / 0 °C

6: 10percent H₂SO₄ / H₂O; tetrahydrofuran / 0.5 h / Ambient temperature

7: 310 mg / PBr₃, pyridine / diethyl ether / 0.33 h / -20 °C

8: 2) p-toluenesulfonic acid, H₃PO₄ / 1) CH₂Cl₂, reflux, 2 h, 2) MeOH, RT, 18 h

9: 1) NaOMe, 2) 1.5M H₂SO₄ / 1) CH₂Cl₂, RT, 20 min, 2) acetone, RT, 20 min

With pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; phosphoric acid; sulfuric acid; sodium methylate; phosphorus tribromide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water;

DOI:10.1248/cpb.36.3328

Reference yield:

4,4-dimethoxy-3-methyl-but-2-en-1-al (62285-97-6) → (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal (122203-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / n-BuLi / hexane; diethyl ether / 1.5 h / Ambient temperature

2: 7.15 g / lithium aluminium hydrid / diethyl ether / 0.5 h / 0 °C

3: 10percent H₂SO₄ / H₂O; tetrahydrofuran / 0.5 h / Ambient temperature

4: 310 mg / PBr₃, pyridine / diethyl ether / 0.33 h / -20 °C

5: 2) p-toluenesulfonic acid, H₃PO₄ / 1) CH₂Cl₂, reflux, 2 h, 2) MeOH, RT, 18 h

6: 1) NaOMe, 2) 1.5M H₂SO₄ / 1) CH₂Cl₂, RT, 20 min, 2) acetone, RT, 20 min

With pyridine; lithium aluminium tetrahydride; n-butyllithium; phosphoric acid; sulfuric acid; sodium methylate; phosphorus tribromide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; water;

DOI:10.1248/cpb.36.3328

Reference yield:

(E)-4-Hydroxy-2-methyl-2-butenal-dimethylacetal (65527-81-3) → (2E,4E,6Z,8E)-11-(4-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-2,9-dimethyl-undeca-2,4,6,8-tetraen-10-ynal (122203-78-5)

Guidance literature:

Multi-step reaction with 7 steps

1: MnO₂ / CH₂Cl₂ / 20 h / Ambient temperature

2: 95 percent / n-BuLi / hexane; diethyl ether / 1.5 h / Ambient temperature

3: 7.15 g / lithium aluminium hydrid / diethyl ether / 0.5 h / 0 °C

4: 10percent H₂SO₄ / H₂O; tetrahydrofuran / 0.5 h / Ambient temperature

5: 310 mg / PBr₃, pyridine / diethyl ether / 0.33 h / -20 °C

6: 2) p-toluenesulfonic acid, H₃PO₄ / 1) CH₂Cl₂, reflux, 2 h, 2) MeOH, RT, 18 h

7: 1) NaOMe, 2) 1.5M H₂SO₄ / 1) CH₂Cl₂, RT, 20 min, 2) acetone, RT, 20 min

With pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; phosphoric acid; sulfuric acid; sodium methylate; phosphorus tribromide; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;

DOI:10.1248/cpb.36.3328

upstream raw materials:

(2E)-5-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methylpent-2-en-4-yn-1-al

((2E,4E)-6,6-Dimethoxy-5-methyl-hexa-2,4-dienyl)-triphenyl-phosphonium; bromide

methyl (E)-3-formylcrotonate

4,4-dimethoxy-3-methyl-but-2-en-1-al

Refernces