(2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate

Base Information

• Chemical Name: (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate
• CAS No.: 388075-83-0
• Molecular Formula: C₂₂H₃₃BrO₂
• Molecular Weight: 409.407
• Mol file: 388075-83-0.mol

Synonyms:(2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate

Chemical Property of (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate

There total 4 articles about (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate 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:

(2E,6E,8E)-4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatriene acetate (388075-82-9) → (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate (388075-83-0)

Guidance literature:

With phosphorus tribromide; In dichloromethane; at -75 - 25 ℃;

DOI:10.1002/1099-0690(200110)2001:20<3903::AID-EJOC3903>3.0.CO;2-R

Reference yield:

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) → (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate (388075-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrobiohenyllithium in THF

1.2: 28 percent / tetrahydrofuran / 0.25 h / -75 °C

2.1: PBr₃ / CH₂Cl₂ / -75 - 25 °C

With hydrobiohenyllithium in THF; phosphorus tribromide; In dichloromethane;

DOI:10.1002/1099-0690(200110)2001:20<3903::AID-EJOC3903>3.0.CO;2-R

Reference yield:

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol (59057-30-6) → (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate (388075-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / NaH / tetrahydrofuran / 1 h / Heating

2.1: hydrobiohenyllithium in THF

2.2: 28 percent / tetrahydrofuran / 0.25 h / -75 °C

3.1: PBr₃ / CH₂Cl₂ / -75 - 25 °C

With hydrobiohenyllithium in THF; phosphorus tribromide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1099-0690(200110)2001:20<3903::AID-EJOC3903>3.0.CO;2-R

upstream raw materials:

(2E,6E,8E)-4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatriene acetate

(E)-4-acetoxy-2-methylcrotonaldehyde

(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

2-[(E)-3-methoxy-3-methyl-1,4-pentadienyl]-1,3,3-trimethylcyclohexene

Downstream raw materials:

Retinol acetate