(E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid

Base Information

• Chemical Name: (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid
• CAS No.: 204063-23-0
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 204063-23-0.mol

Synonyms:(E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid

Chemical Property of (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid

There total 3 articles about (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid 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:

carbon dioxide (124-38-9,18923-20-1) + (E)-5-(2,6,6-trimethylcyclohex-1-enyl)pent-4-en-2-yn-1-ol (101315-21-3) → (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid (204063-23-0)

Guidance literature:

With 2-methylpropylmagnesium chloride; bis(cyclopentadienyl)titanium dichloride; Yield given. Multistep reaction; 1.) ether; 2.) THF;

DOI:10.1016/S0040-4039(97)10805-X

Reference yield:

(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene (73395-75-2) → (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid (204063-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -55 deg C, 50 min, 2.) -55 deg C to room temperature, room temperature, 1 h

2: 1.) iBuMgCl, Cp₂TiCl₂ / 1.) Et₂O, 0 deg C to room temperature, room temperature, 6 h, 2.) THF, 0 deg C, 12 h

With bis(cyclopentadienyl)titanium dichloride; n-butyllithium; 2-methylpropylmagnesium chloride; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(98)01197-1

Reference yield:

(E)-β-ionone (79-77-6,14901-07-6) → (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoic acid (204063-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA, ClP(O)(OEt)2; 2.) n-BuLi / 1.) THF; 2.) THF

2: 1.) iBuMgCl / 1.) Cp₂TiCl₂ / 1.) ether; 2.) THF

With n-butyllithium; 2-methylpropylmagnesium chloride; diethyl chlorophosphate; lithium diisopropyl amide; bis(cyclopentadienyl)titanium dichloride;

DOI:10.1016/S0040-4039(97)10805-X

upstream raw materials:

carbon dioxide

(E)-5-(2,6,6-trimethylcyclohex-1-enyl)pent-4-en-2-yn-1-ol

(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene

(E)-β-ionone

Downstream raw materials:

methyl (E,E)-4-hydroxy-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoate

(E,E)-4-oxo-2-[(2,6,6-trimethylcyclohex-1-enyl)vinyl]but-2-enoic acid

N-n-propyl (E,E)-4-oxo-2-[(2,6,6-trimethylcyclohex-1-enyl)vinyl]but-2-enamide

methyl (E,E)-4-oxo-2-<2-(2,6,6-trimethylcyclohex-1-enyl)vinyl>but-2-enoate