BUTYRIC ACID, p-METHOXYPHENYL ESTER

Base Information

• Chemical Name: BUTYRIC ACID, p-METHOXYPHENYL ESTER
• CAS No.: 14617-95-9
• Molecular Formula: C11H14 O3
• Molecular Weight: 194.23
• DSSTox Substance ID: DTXSID00163280
• Nikkaji Number: J104.016B
• Wikidata: Q83032164
• Mol file: 14617-95-9.mol

Synonyms:(4-methoxyphenyl) butanoate;BUTYRIC ACID, p-METHOXYPHENYL ESTER;4-Methoxyphenyl butyrate;14617-95-9;Anisyl n-butyrate;p-methoxyphenyl n-butyrate;SCHEMBL357271;DTXSID00163280;Butanoic acid 4-methoxyphenyl ester;Butyric acid, 4-methoxyphenyl ester;AKOS002953752;LS-48101;Butanoic acid,(4-methoxyphenyl)methyl ester

Chemical Property of BUTYRIC ACID, p-METHOXYPHENYL ESTER

Chemical Property:

• Vapor Pressure: 0.0038mmHg at 25°C
• Refractive Index: 1.5040 (estimate)
• Boiling Point: 280.4°Cat760mmHg
• Flash Point: 112.6°C
• PSA: 35.53000
• Density: 1.055g/cm³
• LogP: 2.40070
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)OC1=CC=C(C=C1)OC

Technology Process of BUTYRIC ACID, p-METHOXYPHENYL ESTER

There total 4 articles about BUTYRIC ACID, p-METHOXYPHENYL 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: 92.0%

4-methoxy-phenol (150-76-5) + butyric acid (107-92-6) → 4-methoxyphenyl n-butyrate (14617-95-9)

Guidance literature:

butyric acid; With 7,7-dichlorocyclohepta-1,3,5-triene; triethylamine; In dichloromethane; at 20 ℃; for 0.416667h; Inert atmosphere;

4-methoxy-phenol; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/c4cc09539a

Reference yield:

butyric acid (107-92-6) + 4-methoxy-2-(trimethylsilyl)phenyl triflate (556812-41-0) → 2-Hydroxy-5-methoxy-butyrophenon (57314-81-5) + 3-Methoxyphenylbutyrat (14617-94-8) + 4-methoxyphenyl n-butyrate (14617-95-9)

Guidance literature:

butyric acid; 4-methoxy-2-(trimethylsilyl)phenyl triflate; With sodium hydroxide; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

With cesium fluoride; In acetonitrile; at 80 ℃; for 4h; Overall yield = 63 %; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.08.019

Reference yield:

4-methoxy-phenol (150-76-5) → 4-methoxyphenyl n-butyrate (14617-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 1 h / Ambient temperature

2: N,N-dimethylaniline / 1,2-dichloro-benzene / 24 h / Heating

With N,N-dimethyl-aniline; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dichloro-benzene;

DOI:10.1021/jm00085a019

upstream raw materials:

4-methoxy-phenol

butyric acid

4-methoxy-2-(trimethylsilyl)phenyl triflate

Downstream raw materials:

4-methoxy-phenol

2-(1,1-dimethyl-2,3-epoxypropyl)-4-methoxyphenyl n-butyrate

Refernces

• 1、 Nguyen, Thanh V.,Lyons, Demelza J.M.. "A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions". supporting information. p. 3131 - 3134. Retrieved 2015/06/17.
• 2、 Lau, Cheuk K.,Belanger, Patrice C.,Dufresne, Claude,Scheigetz, John,Therien, Michael,et al.. "Development of 2,3-Dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol (L-670,630) as a Potent and Orally Active Inhibitor of 5-Lipoxygenase". . p. 1299 - 1318. Retrieved 2007/10/02.