(Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol

Base Information

• Chemical Name: (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol
• CAS No.: 783332-55-8
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.311
• Mol file: 783332-55-8.mol

Synonyms:(Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol

Chemical Property of (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol

There total 8 articles about (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol 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 5-(2-methoxy-4-methyl-6-(tetrahydropyran-2-yloxy))-phenyl-3-methylpentanoate → (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol (783332-55-8) + (E)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol (783332-51-4)

Guidance literature:

methyl 5-(2-methoxy-4-methyl-6-(tetrahydropyran-2-yloxy))-phenyl-3-methylpentanoate; With diisobutylaluminium hydride; In diethyl ether; hexane; water; at -78 - 20 ℃; for 1.33333h;

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 1h;

DOI:10.1021/ja048078t

Reference yield:

1,3-dimethoxy-5-methyl-2-vinylbenzene (783332-52-5) → (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol (783332-55-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / rhodium tris(phenylphosphine) chloride / tetrahydrofuran / 20 - 50 °C

2.1: 100 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1.5 h / 50 °C

3.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

4.1: zinc chloride; tert-butyllithium / tetrahydrofuran; pentane / 3.5 h / -78 - 20 °C

4.2: Pd(dppf)Cl₂; n-butyllithium / tetrahydrofuran; pentane; hexane / 20 °C

5.1: TBAF / tetrahydrofuran / 2 h

6.1: 80 percent / lithium n-propyl thiolate / hexamethylphosphoric acid triamide / 120 °C

With 1H-imidazole; sodium hydroxide; Wilkinson's catalyst; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tert.-butyl lithium; lithium n-propylmercaptide; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; 4.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

2-(2,6-dimethoxy-4-methylphenyl)ethanol (783332-53-6) → (Z)-2-(5-hydroxy-3-methylpent-3-enyl)-3-methoxy-5-methylphenol (783332-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

2.1: zinc chloride; tert-butyllithium / tetrahydrofuran; pentane / 3.5 h / -78 - 20 °C

2.2: Pd(dppf)Cl₂; n-butyllithium / tetrahydrofuran; pentane; hexane / 20 °C

3.1: TBAF / tetrahydrofuran / 2 h

4.1: 80 percent / lithium n-propyl thiolate / hexamethylphosphoric acid triamide / 120 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; lithium n-propylmercaptide; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; 2.2: Negishi coupling;

DOI:10.1021/ja048078t

upstream raw materials:

orcinol

1,3-dimethoxy-5-methyl-2-vinylbenzene

2-(2,6-dimethoxy-4-methylphenyl)ethanol

2-(2-iodoethyl)-1,3-dimethoxy-5-methylbenzene

Downstream raw materials:

Carbonic acid (Z)-5-(2-hydroxy-6-methoxy-4-methyl-phenyl)-3-methyl-pent-2-enyl ester methyl ester