(2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

Base Information

• Chemical Name: (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide
• CAS No.: 63184-93-0
• Molecular Formula: Br*C₃₃H₃₆OP
• Molecular Weight: 559.526
• Mol file: 63184-93-0.mol

Synonyms:(2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

Chemical Property of (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

There total 26 articles about (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide 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: 69.0%

3-((1Z,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-2,4,4-trimethyl-cyclohex-2-enone (79749-53-4) + triphenylphosphine (603-35-0) → (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0)

Guidance literature:

In benzene; Heating;

DOI:10.1021/jo00132a028

Reference yield:

1-(2,6,6-Trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-5-bromo-penta-1,3-diene (63184-94-1) + triphenylphosphine (603-35-0) → (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0)

Guidance literature:

In toluene; at 20 ℃; for 24h;

Reference yield:

(E)-3-methylpent-2-en-4-yn-1-ol (6153-06-6,105-29-3) → (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / p-toluenesulfonic acid / 1.) 5 deg C, 2.) RT, 10 min

2: 1.) n-BuLi / 1.) ether, hexane, RT, 15 min, 2.) 22 deg C, 1 h

3: 72 percent / H₂, potassium carbonate / Lindlar catalyst / toluene / 3 h / 20 °C / 760 Torr

4: PBr₃ / diethyl ether / 0.08 h / Ambient temperature

5: 69 percent / benzene / Heating

With n-butyllithium; hydrogen; phosphorus tribromide; potassium carbonate; toluene-4-sulfonic acid; Lindlar's catalyst; In diethyl ether; toluene; benzene;

DOI:10.1021/jo00132a028

upstream raw materials:

triphenylphosphine hydrobromide

5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-3-hydroxy-1,4-pentadiene

3-((1Z,3E)-5-Bromo-3-methyl-penta-1,3-dienyl)-2,4,4-trimethyl-cyclohex-2-enone

triphenylphosphine

Downstream raw materials:

(6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid

Triphenylphosphine oxide

4-ketoretinoic acid

ethyl (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate