2-(2,5-dimethylphenyl)propanoic Acid

Base Information

• Chemical Name: 2-(2,5-dimethylphenyl)propanoic Acid
• CAS No.: 18288-28-3
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.231
• DSSTox Substance ID: DTXSID201301015
• Mol file: 18288-28-3.mol

Synonyms:2-(2,5-dimethylphenyl)propanoic Acid;18288-28-3;SCHEMBL3670597;DTXSID201301015;2-(2,5-dimethylphenyl)propanoicAcid;alpha,2,5-Trimethylbenzeneacetic acid;AKOS010488458;CS-0274799;EN300-1137779

Chemical Property of 2-(2,5-dimethylphenyl)propanoic Acid

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)C)C(C)C(=O)O

Technology Process of 2-(2,5-dimethylphenyl)propanoic Acid

There total 10 articles about 2-(2,5-dimethylphenyl)propanoic Acid 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: 79.0%

carbon dioxide (124-38-9,18923-20-1) + 2,5-dimethylstyrene (2039-89-6) → 2-(2,5-dimethylphenyl)propanoic acid (18288-28-3)

Guidance literature:

2,5-dimethylstyrene; With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride; lithium bromide; In diethyl ether; at 30 ℃; for 24h; Schlenk technique; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at 20 ℃; for 0.5h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00665

Reference yield:

3-<1-(2,5-dimethylphenyl)ethyl>-5,6-dihydro-1,4,2-dioxazine (128228-14-8) → 2-(2,5-dimethylphenyl)propanoic acid (18288-28-3)

Guidance literature:

With hydrogenchloride; In methanol; at 65 ℃; for 10h;

DOI:10.1039/c39900000327

Reference yield:

(2,5-dimethyl-phenyl)-hydroxy-malonic acid diethyl ester (83026-12-4) → 2-(2,5-dimethylphenyl)propanoic acid (18288-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 20 °C

2: 1.) sodium α-(dimethylamino)naphthalenide / 1.) benzene, HMPA, 30 s, 2.) 30 min

3: 1.) KOH/H₂O, 2.) conc. HCl / 1.) reflux, 4 h, 2.) reflux, 2 h

With hydrogenchloride; dmap; potassium hydroxide; sodium α-(dimethylamino)naphthalenide; water; triethylamine; In dichloromethane;

DOI:10.1021/jo00145a017

upstream raw materials:

3-<1-(2,5-dimethylphenyl)ethyl>-5,6-dihydro-1,4,2-dioxazine

diethyl (2,5-dimethylphenyl)methylpropanedioate

2-(2,5-dimethyl-phenyl)-acrylic acid

(2,5-dimethyl-phenyl)-hydroxy-malonic acid diethyl ester

Downstream raw materials:

(R)-2-(2,5-dimethylphenyl)propanoic acid

di(1-naphthyl)methyl (S)-2-(2,5-dimethylphenyl)propanoate

Refernces

• 1、 Wang, Dinghai,Zhu, Na,Chen, Pinhong,Lin, Zhenyang,Liu, Guosheng. "Enantioselective Decarboxylative Cyanation Employing Cooperative Photoredox Catalysis and Copper Catalysis". supporting information. p. 15632 - 15635. Retrieved 2017/11/14.
• 2、 Shatzmiller, Shimon,Bercovici, Sorin. "The Generation and Use of Masked α-Acyl Cation in Aromatic Substitution Reactions; Ag+ induced Reactions of 3-(Bromomethyl)-5,6-dihydro-1,4,2-dioxazine Derivatives". . p. 327 - 328. Retrieved 2007/10/02.