4-(Carboxymethyl)-2-ethoxybenzoic acid

Base Information

• Chemical Name: 4-(Carboxymethyl)-2-ethoxybenzoic acid
• CAS No.: 220438-80-2
• Molecular Formula: C11H12O5
• Molecular Weight: 224.213
• Hs Code.: 2918990090
• UNII: P92FSD7933
• DSSTox Substance ID: DTXSID50176522
• Wikidata: Q27286393
• Mol file: 220438-80-2.mol

Synonyms:4-(CARBOXYMETHYL)-2-ETHOXYBENZOIC ACID;220438-80-2;(4-Carboxy-3-ethoxy)phenyl Acetic Acid;(4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide Impurity);Benzeneacetic acid, 4-carboxy-3-ethoxy-;P92FSD7933;4-Carboxymethyl-2-ethoxybenzoic acid;UNII-P92FSD7933;SCHEMBL3225523;DTXSID50176522;AKOS024260785;Repaglinide specified impurity A [EP];REPAGLINIDE IMPURITY A [EP IMPURITY];4-(CARBOXYMETHYL)-2-ETHOXYBENZOICACID;J-014442;Q27286393;4-Carboxy-3-ethoxybenzeneacetic Acid Repaglinide Impurity;4-(CARBOXYMETHYL)-2-ETHOXYBENZOIC ACID [USP IMPURITY]

Chemical Property of 4-(Carboxymethyl)-2-ethoxybenzoic acid

Chemical Property:

• Melting Point: 140-142?C
• Boiling Point: 428.1±35.0 °C(Predicted)
• PKA: 3.96±0.10(Predicted)
• PSA: 83.83000
• Density: 1.319±0.06 g/cm3(Predicted)
• LogP: 1.41060
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 224.06847348
• Heavy Atom Count: 16
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

(4-Carboxy-3-ethoxy)phenylAceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=CC(=C1)CC(=O)O)C(=O)O
• Uses: Repaglinide (4-Carboxy-3-ethoxy)phenyl Acetic Acid (Repaglinide EP Impurity A) is a Repaglinide impurity.

Technology Process of 4-(Carboxymethyl)-2-ethoxybenzoic acid

There total 9 articles about 4-(Carboxymethyl)-2-ethoxybenzoic 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: 96.0%

ethyl 4-cyanomethyl-2-ethoxy-benzoate (99470-01-6) → 2-ethoxy-[4-(carboxymethyl)]benzoic acid (220438-80-2)

Guidance literature:

ethyl 4-cyanomethyl-2-ethoxy-benzoate; With sodium hydroxide; water; for 1.5 - 2h; Heating / reflux;

With hydrogenchloride; In water; at 25 - 35 ℃; for 0.75 - 1h; pH=2;

Reference yield: 86.6%

2-(3-ethoxy-4-(methoxycarbonyl)phenyl)acetic acid (503834-19-3) → 2-ethoxy-[4-(carboxymethyl)]benzoic acid (220438-80-2)

Guidance literature:

With sodium hydroxide; In water; for 4h; Reflux;

DOI:10.1007/s10870-019-00811-7

Reference yield: 65.0%

carbon dioxide (124-38-9,18923-20-1) + 4-bromomethyl-2-ethoxybromobenzene → 2-ethoxy-[4-(carboxymethyl)]benzoic acid (220438-80-2)

Guidance literature:

4-bromomethyl-2-ethoxybromobenzene; With iodine; magnesium; In tetrahydrofuran; at 40 - 60 ℃; for 18h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at 0 ℃; for 5h;

upstream raw materials:

2-hydroxy-p-toluic acid

ethyl 2-ethoxy-4-methyl-benzoate

ethyl 4-bromomethyl-2-ethoxy-benzoate

ethyl 4-cyanomethyl-2-ethoxy-benzoate

Downstream raw materials:

ethyl 2-ethoxy-4-ethoxycarbonylmethyl-benzoate

C₂₇H₃₆N₂O₄

Refernces

• 1、 Tang, Gui-Mei,Wang, Yong-Tao,Wu, Yu-Song. "Preparation, Characterization and Crystal Structures of a Key Intermediate, and a Significant Impurity, in the Synthesis of Repaglinide". . p. 381 - 386. Retrieved 2020.
• 2、 Sundaram, Dhanraj T. S. S.,Mitra, Jayati,Rajesh,Islam, Aminul,Prabahar, Koilpillai Joseph,Rao, Battula Venkateswara,Douglas, Sanasi Paul. "Synthesis of Repaglinide Congeners". . p. 2092 - 2098. Retrieved 2015/09/01.