Carbonic acid, (2Z)-5-(2-hydroxy-6-methoxy-4-methylphenyl)-3-methyl-2-pentenyl methyl ester

Base Information

• Chemical Name: Carbonic acid, (2Z)-5-(2-hydroxy-6-methoxy-4-methylphenyl)-3-methyl-2-pentenyl methyl ester
• CAS No.: 593251-76-4
• Molecular Formula: C16H22O5
• Molecular Weight: 294.348
• Mol file: 593251-76-4.mol

Synonyms:

Chemical Property of Carbonic acid, (2Z)-5-(2-hydroxy-6-methoxy-4-methylphenyl)-3-methyl-2-pentenyl methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbonic acid, (2Z)-5-(2-hydroxy-6-methoxy-4-methylphenyl)-3-methyl-2-pentenyl methyl ester

There total 9 articles about Carbonic acid, (2Z)-5-(2-hydroxy-6-methoxy-4-methylphenyl)-3-methyl-2-pentenyl methyl ester 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:

1,3-dimethoxy-5-methylbenzene (4179-19-5) → Carbonic acid (Z)-5-(2-hydroxy-6-methoxy-4-methyl-phenyl)-3-methyl-pent-2-enyl ester methyl ester (593251-76-4)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: 97 percent / diethyl ether / 2 h / 20 °C

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

2.2: 98 percent / tetrahydrofuran / -78 - 20 °C

3.1: 85 percent / rhodium tris(phenylphosphine) chloride / tetrahydrofuran / 20 - 50 °C

4.1: 100 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1.5 h / 50 °C

5.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

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

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

7.1: TBAF / tetrahydrofuran / 2 h

8.1: 80 percent / lithium n-propyl thiolate / hexamethylphosphoric acid triamide / 120 °C

9.1: pyridine / CH₂Cl₂

With pyridine; 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; lithium n-propylmercaptide; triphenylphosphine; zinc(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; pentane; 6.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

1,3-dimethoxy-5-methyl-2-vinylbenzene (783332-52-5) → Carbonic acid (Z)-5-(2-hydroxy-6-methoxy-4-methyl-phenyl)-3-methyl-pent-2-enyl ester methyl ester (593251-76-4)

Guidance literature:

Multi-step reaction with 7 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

7.1: pyridine / CH₂Cl₂

With pyridine; 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; dichloromethane; pentane; 4.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

2-(2,6-dimethoxy-4-methylphenyl)ethanol (783332-53-6) → Carbonic acid (Z)-5-(2-hydroxy-6-methoxy-4-methyl-phenyl)-3-methyl-pent-2-enyl ester methyl ester (593251-76-4)

Guidance literature:

Multi-step reaction with 5 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

5.1: pyridine / CH₂Cl₂

With pyridine; 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; dichloromethane; pentane; 2.2: Negishi coupling;

DOI:10.1021/ja048078t

upstream raw materials:

methyl chloroformate

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

1,3-dimethoxy-5-methylbenzene

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

Downstream raw materials:

(1S)-2-[2-(2,2-dimethyl-6-methylenecyclohexyl)vinyl]-(2R)-5-methoxy-2,7-dimethylchroman

Toluene-4-sulfonic acid (1S,2S)-1-hydroxy-2-[2-((S)-5-methoxy-2,7-dimethyl-2H-chromen-2-yl)-ethyl]-3,3-dimethyl-cyclohexylmethyl ester

(1S,2S)-1-hydroxymethyl-2-[(2S)-2-(5-methoxy-2,7-dimethyl-2H-chromen-2-yl)ethyl]-3,3-dimethylcyclohexanol

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