(E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate

Base Information

• Chemical Name: (E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate
• CAS No.: 1390642-45-1
• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.338
• Mol file: 1390642-45-1.mol

Synonyms:(E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate

Chemical Property of (E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate

There total 1 articles about (E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate 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: 55.0%

methanol (67-56-1) + 7-benzyloxy-8-methoxycoumarin (65535-52-6) → (E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate (1390642-45-1)

Guidance literature:

With sodium methylate; at 65 ℃; for 13h; Inert atmosphere;

DOI:10.1021/ol301893t

Reference yield:

(E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate (1390642-45-1) + isopropyl bromide (75-26-3) → (E)-methyl 3-(4-(benzyloxy)-2-isopropoxy-3-methoxyphenyl)acrylate (1390642-33-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol301893t

Reference yield:

(E)-methyl 3-(4-(benzyloxy)-2-hydroxy-3-methoxyphenyl)acrylate (1390642-45-1) → 1-(3-bromo-4-isopropoxyphenyl)-7-(4-hydroxy-2-isopropoxy-3-methoxyphenyl)heptan-3-one (1390642-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / -78 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.25 h / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.17 h / Inert atmosphere

4.2: 18 h / 60 °C / Inert atmosphere

5.1: 20 % Pd(OH)2/C; hydrogen / water; ethyl acetate / 2 h / Inert atmosphere

With 20 % Pd(OH)2/C; hydrogen; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 4.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/ol301893t

upstream raw materials:

methanol

7-benzyloxy-8-methoxycoumarin

Downstream raw materials:

1-(3-bromo-4-isopropoxyphenyl)-7-(4-hydroxy-2-isopropoxy-3-methoxyphenyl)heptan-3-one

1-(3-bromo-4-methoxyphenyl)-7-(4-hydroxy-2-isopropoxy-3-methoxyphenyl)heptan-3-one

(2E)-3-(4-(benzyloxy)-3-methoxy-2-(isopropoxy)phenyl)prop-2-en-1-ol

(E)-3-(4-(benzyloxy)-2-isopropoxy-3-methoxyphenyl)acrylaldehyde