acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester

Base Information

• Chemical Name: acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester
• CAS No.: 290362-01-5
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.423
• Mol file: 290362-01-5.mol

Synonyms:acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester

Chemical Property of acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester

There total 6 articles about acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl 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: 76.0%

2,4-diacetoxybenzaldehyde (41777-08-6) + (2-Benzo[1,3]dioxol-5-ylmethyl-buta-2,3-dienyl)-trimethyl-silane (201345-85-9) → acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester (290362-01-5)

Guidance literature:

With titanium tetrachloride; acetonitrile; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)00604-3

Reference yield:

piperonal (120-57-0,30024-74-9) → acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester (290362-01-5)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / -78 °C

2: Et₃N; DMAP / CH₂Cl₂

3: 69 percent / Et₃SiH; TFA / CH₂Cl₂ / -20 °C

4: 86 percent / n-BuLi / tetrahydrofuran / -40 °C

5: 89 percent / CuCN; LiCl / tetrahydrofuran / -40 °C

6: 76 percent / TiCl₄; CH₃CN / CH₂Cl₂ / -78 °C

With triethylsilane; dmap; n-butyllithium; titanium tetrachloride; triethylamine; acetonitrile; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Acetylation / 3: Reduction / 4: Tosylation / 5: Addition / 6: Addition;

DOI:10.1016/S0040-4039(00)00604-3

Reference yield:

Toluene-4-sulfonic acid 4-benzo[1,3]dioxol-5-yl-but-2-ynyl ester (201345-78-0) → acetic acid 1-(4-acetoxy-2-hydroxy-phenyl)-3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl ester (290362-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / CuCN; LiCl / tetrahydrofuran / -40 °C

2: 76 percent / TiCl₄; CH₃CN / CH₂Cl₂ / -78 °C

With titanium tetrachloride; acetonitrile; lithium chloride; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Addition;

DOI:10.1016/S0040-4039(00)00604-3

upstream raw materials:

2,4-diacetoxybenzaldehyde

(2-Benzo[1,3]dioxol-5-ylmethyl-buta-2,3-dienyl)-trimethyl-silane

piperonal

4-Benzo[1,3]dioxol-5-yl-but-2-yn-1-ol

Downstream raw materials:

anolignan A

acetic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl)-3-hydroxy-phenyl ester