(E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol

Base Information

• Chemical Name: (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol
• CAS No.: 783332-56-9
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 783332-56-9.mol

Synonyms:(E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol

Chemical Property of (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol

There total 6 articles about (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol 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:

tert-butyl-[5-(2,6-dimethoxy-4-methyl-phenyl)-3-methyl-pent-2-enyloxy]-dimethyl-silane → (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol (783332-56-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1021/ja048078t

Reference yield:

orcinol (504-15-4) → (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol (783332-56-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: K₂CO₃ / acetone

2.1: tetramethylene diamine; n-butyllithium / diethyl ether / 3 h / Heating

2.2: 97 percent / diethyl ether / 2 h / 20 °C

3.1: sodium bis(trimethylsilyl)amine / tetrahydrofuran / 3 h / 20 °C

3.2: 98 percent / tetrahydrofuran / -78 - 20 °C

4.1: 85 percent / rhodium tris(phenylphosphine) chloride / tetrahydrofuran / 20 - 50 °C

5.1: 100 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1.5 h / 50 °C

6.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

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

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

8.1: 78 mg / TBAF / tetrahydrofuran / 1 h

With 1H-imidazole; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; potassium carbonate; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; acetone; pentane; 7.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

1,3-dimethoxy-5-methyl-2-vinylbenzene (783332-52-5) → (E)-5-(2,6-dimethoxy-4-methylphenyl)-2-methyl-pent-2-en-1-ol (783332-56-9)

Guidance literature:

Multi-step reaction with 5 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: 78 mg / TBAF / tetrahydrofuran / 1 h

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

(R)-2-(5-methoxymethoxy-2,7-dimethylchroman-2-yl)-ethyl-tert-butyldiphenylsilyl ether

(R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane

(R)-2,7-dimethyl-2-vinylchroman-1-ol

(E)-5-(2-hydroxy-6-methoxyphenyl)-3-methylpent-2-enyl methyl carbonate