3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate

Base Information

• Chemical Name: 3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate
• CAS No.: 145904-50-3
• Molecular Formula: C18H16 O7
• Molecular Weight: 344.3154
• Nikkaji Number: J514.323C
• Mol file: 145904-50-3.mol

Synonyms:3-(3,4-dihydroxyphenyl)-2-oxopropyl caffeate;petasiphenol

Chemical Property of 3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate

Chemical Property:

• Vapor Pressure: 4.3E-16mmHg at 25°C
• Boiling Point: 622.6°Cat760mmHg
• Flash Point: 228.4°C
• PSA: 124.29000
• Density: 1.465g/cm³
• LogP: 1.87720
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 344.08960285
• Heavy Atom Count: 25
• Complexity: 490

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(=O)COC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1CC(=O)COC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O

Technology Process of 3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate

There total 6 articles about 3-(3,4-Dihydroxyphenyl)-2-oxopropyl caffeate 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: 89.0%

(E)-3-(3,4-Bis-methoxymethoxy-phenyl)-acrylic acid 3-(3,4-bis-methoxymethoxy-phenyl)-2-oxo-propyl ester (145904-57-0) → Petasiphenol (145904-50-3)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 65 ℃; for 48h;

DOI:10.1271/bbb.56.1773

Reference yield:

3,4-Bis(methoxymethoxy)phenylmagnesium bromide (145904-61-6) → Petasiphenol (145904-50-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.5 h / 55 °C

2: 37.1 percent / mCPBA / CH₂Cl₂ / 24 h

3: 100 percent / HBr, LiBr / diethyl ether / -20 - -15 °C

4: 91.3 percent / dimethylformamide; hexamethylphosphoric acid triamide / 8 h / 85 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -20 deg C, 30 min, 2) r.t., 20 min

6: 89 percent / p-TsOH / aq. ethanol / 48 h / 65 °C

With oxalyl dichloride; hydrogen bromide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb.56.1773

Reference yield:

4-Allyl-1,2-bis-methoxymethoxy-benzene (145904-60-5) → Petasiphenol (145904-50-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 37.1 percent / mCPBA / CH₂Cl₂ / 24 h

2: 100 percent / HBr, LiBr / diethyl ether / -20 - -15 °C

3: 91.3 percent / dimethylformamide; hexamethylphosphoric acid triamide / 8 h / 85 °C

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -20 deg C, 30 min, 2) r.t., 20 min

5: 89 percent / p-TsOH / aq. ethanol / 48 h / 65 °C

With oxalyl dichloride; hydrogen bromide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb.56.1773

upstream raw materials:

(E)-3-(3,4-Bis-methoxymethoxy-phenyl)-acrylic acid 3-(3,4-bis-methoxymethoxy-phenyl)-2-oxo-propyl ester

3,4-Bis(methoxymethoxy)phenylmagnesium bromide

4-Allyl-1,2-bis-methoxymethoxy-benzene

4-(2,3-Epoxypropyl)catechol di(methoxymethyl)ether

Downstream raw materials:

Petasiphenol pentaacetate

Refernces