(E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one

Base Information

• Chemical Name: (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one
• CAS No.: 1447962-89-1
• Molecular Formula: C₂₁H₁₉NO₄
• Molecular Weight: 349.386
• Mol file: 1447962-89-1.mol

Synonyms:(E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one

Chemical Property of (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one

There total 2 articles about (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one 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: 81.0%

6-acetyl-7-hydroxy-4-methylcoumarin (16555-98-9) + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one (1447962-89-1)

Guidance literature:

With piperidine; In ethanol; Reflux;

DOI:10.1139/cjc-2013-0053

Reference yield:

4-methylumbelliferyl acetate (2747-05-9) → (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one (1447962-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / 2 h / 125 - 170 °C

2: piperidine / ethanol / Reflux

With piperidine; aluminum (III) chloride; In ethanol; 1: |Fries Phenol Ester Rearrangement / 2: |Claisen-Schmidt Condensation;

DOI:10.1139/cjc-2013-0053

Reference yield: 89.0%

(E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one (1447962-89-1) + methyl iodide (74-88-4) → (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-7-methoxy-4-methyl-2H-chromen-2-one

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 30 ℃;

DOI:10.1016/j.jphotochem.2014.02.005

upstream raw materials:

6-acetyl-7-hydroxy-4-methylcoumarin

4-dimethylamino-benzaldehyde

4-methylumbelliferyl acetate