methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate

Base Information

• Chemical Name: methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate
• CAS No.: 187339-59-9
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 320.444
• Mol file: 187339-59-9.mol

Synonyms:

Chemical Property of methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate

There total 7 articles about methyl-(2E,4E,6Z,8E)-3-³H₃C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate 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:

(Z)-3-methylpent-2-en-4-ynol (6153-05-5,105-29-3) → methyl-(2E,4E,6Z,8E)-3-3H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate (187339-59-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) ethylmagnesium bromide / 1.) THF, Et₂O, RT, 30 min, 2.) THF, Et₂O, overnight

2: 68 percent / LAH / tetrahydrofuran / Ambient temperature

3: 79 percent / MnO₂ / CH₂Cl₂ / Ambient temperature

4: 75 percent / benzene

5: 69 percent / 80percent aq. HCOOH / hexane / Ambient temperature

6: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

7: 74 percent / MnO₂ / CH₂Cl₂

8: tetrahydrofuran; diethyl ether / 2 h / 0 °C

9: MnO₂ / CH₂Cl₂ / 1 h / Ambient temperature

10: 1.) NaH / 1.) THF, RT, 15 min 2.) THF, RT, 18 h

With manganese(IV) oxide; lithium aluminium tetrahydride; formic acid; ethylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1002/(SICI)1099-1344(199701)39:1<1::AID-JLCR939>3.0.CO;2-A

Reference yield:

9-cis-β-ionylidenecrotonaldehyde (67567-19-5) → methyl-(2E,4E,6Z,8E)-3-3H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate (187339-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 2 h / 0 °C

2: MnO₂ / CH₂Cl₂ / 1 h / Ambient temperature

3: 1.) NaH / 1.) THF, RT, 15 min 2.) THF, RT, 18 h

With manganese(IV) oxide; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/(SICI)1099-1344(199701)39:1<1::AID-JLCR939>3.0.CO;2-A

Reference yield:

(2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-ol (187339-51-1) → methyl-(2E,4E,6Z,8E)-3-3H3C,7-methyl-9-(2,2,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoate (187339-59-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / MnO₂ / CH₂Cl₂ / Ambient temperature

2: 75 percent / benzene

3: 69 percent / 80percent aq. HCOOH / hexane / Ambient temperature

4: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

5: 74 percent / MnO₂ / CH₂Cl₂

6: tetrahydrofuran; diethyl ether / 2 h / 0 °C

7: MnO₂ / CH₂Cl₂ / 1 h / Ambient temperature

8: 1.) NaH / 1.) THF, RT, 15 min 2.) THF, RT, 18 h

With manganese(IV) oxide; formic acid; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1002/(SICI)1099-1344(199701)39:1<1::AID-JLCR939>3.0.CO;2-A

upstream raw materials:

(Z)-3-methylpent-2-en-4-ynol

9-cis-β-ionylidenecrotonaldehyde

(2Z,4E)-3-methyl-5-(1-hydroxy-2,2,6-trimethylcyclohexyl)-pent-2,4-dien-1-ol

(2E,4Z,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trien-1-ol