(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester

Base Information

• Chemical Name: (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester
• CAS No.: 377047-67-1
• Molecular Formula: C₂₂H₂₀O₇
• Molecular Weight: 396.397
• Mol file: 377047-67-1.mol

Synonyms:(E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester

Chemical Property of (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester

There total 4 articles about (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-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: 53.0%

4-acetoxycinnamic acid (27542-85-4) + (E)-1-Hydroxy-4-(4-hydroxy-3-methoxy-phenyl)-but-3-en-2-one (336784-86-2) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester (377047-67-1)

Guidance literature:

With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide; In chloroform; at 20 ℃;

DOI:10.1016/S0960-894X(01)00489-9

Reference yield:

3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde (91471-08-8) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester (377047-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 27 percent / tetrahydrofuran

2.1: 42 percent / PPTS / methanol / 50 °C

3.1: 53 percent / DCC; DMAP; DMAP*HCl / CHCl₃ / 20 °C

With dmap; 4-(dimethylamino)pyridine hydrochloride; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0960-894X(01)00489-9

Reference yield:

vanillin (121-33-5,8014-42-4) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (E)-4-(4-hydroxy-3-methoxy-phenyl)-2-oxo-but-3-enyl ester (377047-67-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / PPTS / tetrahydrofuran

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 27 percent / tetrahydrofuran

3.1: 42 percent / PPTS / methanol / 50 °C

4.1: 53 percent / DCC; DMAP; DMAP*HCl / CHCl₃ / 20 °C

With dmap; 4-(dimethylamino)pyridine hydrochloride; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0960-894X(01)00489-9

upstream raw materials:

4-acetoxycinnamic acid

(E)-1-Hydroxy-4-(4-hydroxy-3-methoxy-phenyl)-but-3-en-2-one

3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde

vanillin