Benzoic acid, 4-[5,5-dicyano-3-(ethoxymethylene)-4-pentenyl]-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 4-[5,5-dicyano-3-(ethoxymethylene)-4-pentenyl]-, methyl ester
• CAS No.: 123910-84-9
• Molecular Formula: C₁₈H₁₈N₂O₃
• Molecular Weight: 310.353
• Mol file: 123910-84-9.mol

Synonyms:

Chemical Property of Benzoic acid, 4-[5,5-dicyano-3-(ethoxymethylene)-4-pentenyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid, 4-[5,5-dicyano-3-(ethoxymethylene)-4-pentenyl]-, methyl ester

There total 5 articles about Benzoic acid, 4-[5,5-dicyano-3-(ethoxymethylene)-4-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: 54.0%

Methyl 4-(5,5-dicyano-4-pentenyl)benzoate (123910-83-8) + orthoformic acid triethyl ester (122-51-0) → Methyl 4-<5,5-dicyano-3-(ethoxymethylidene)-4-pentenyl>benzoate (123910-84-9) + 4-(5,5-Dicyano-3-diethoxymethyl-pent-4-enyl)-benzoic acid methyl ester (126295-74-7)

Guidance literature:

With acetic anhydride; zinc(II) chloride; a) 145 deg C, 18 h b) 150 deg C, 12 h;

DOI:10.1021/jo00297a044

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) → Methyl 4-<5,5-dicyano-3-(ethoxymethylidene)-4-pentenyl>benzoate (123910-84-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / palladium chloride, triphenylphosphine, copper(I) iodide, diethylamine / 18 h / Ambient temperature

2: 100 percent / hydrogen / 5percent Pd/C / ethanol / 12 h / 2585.7 Torr

3: 60 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 12 h / Ambient temperature

4: 75 percent / DL-alanine / acetic acid; benzene / 3 h / Heating

5: 54 percent / acetic anhydride, zinc chloride / a) 145 deg C, 18 h b) 150 deg C, 12 h

With copper(l) iodide; hydrogen; sodium acetate; acetic anhydride; diethylamine; triphenylphosphine; rac-Ala-OH; pyridinium chlorochromate; palladium dichloride; zinc(II) chloride; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00297a044

Reference yield:

4-(4-hydroxybut-1-ynyl)benzoic acid methyl ester (123910-86-1) → Methyl 4-<5,5-dicyano-3-(ethoxymethylidene)-4-pentenyl>benzoate (123910-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / hydrogen / 5percent Pd/C / ethanol / 12 h / 2585.7 Torr

2: 60 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / DL-alanine / acetic acid; benzene / 3 h / Heating

4: 54 percent / acetic anhydride, zinc chloride / a) 145 deg C, 18 h b) 150 deg C, 12 h

With hydrogen; sodium acetate; acetic anhydride; rac-Ala-OH; pyridinium chlorochromate; zinc(II) chloride; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid; benzene;

DOI:10.1021/jo00297a044

upstream raw materials:

Methyl 4-(5,5-dicyano-4-pentenyl)benzoate

orthoformic acid triethyl ester

4-methoxycarbonylphenyl bromide

methyl 4-(4-hydroxybut-1-yl)benzoate

Downstream raw materials:

Methyl 5,10-dideazapteroate

5,10-Dideazapteroic acid