2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic acid

Base Information

• Chemical Name: 2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic acid
• CAS No.: 72619-35-3
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.311
• DSSTox Substance ID: DTXSID101203414
• Mol file: 72619-35-3.mol

Synonyms:2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic acid;SCHEMBL11335192;DTXSID101203414;72619-35-3

Chemical Property of 2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic acid

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 300.09977361
• Heavy Atom Count: 22
• Complexity: 387

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)OC2=CC=C(C=C2)CC(=O)O)CC(=O)O

Technology Process of 2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic acid

There total 6 articles about 2-[4-(Carboxymethyl)phenoxy]-5-methylbenzeneacetic 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: 73.0%

[2-(4-Cyanomethyl-phenoxy)-5-methyl-phenyl]-acetonitrile (82340-89-4) → 4-(2'-carboxymethyl-4'-methylphenoxy)phenylacetic acid (72619-35-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 16h; Heating;

DOI:10.1021/jm00351a012

Reference yield:

Ethyl 4-hydroxybenzoate (120-47-8) → 4-(2'-carboxymethyl-4'-methylphenoxy)phenylacetic acid (72619-35-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / K₂CO₃, Cu / nitrobenzene / 0.5 h / 140 - 150 °C

2: LiAlH₄ / tetrahydrofuran / 4 h / Heating

3: SOCl₂ / CHCl₃ / 1 h / Heating

4: dioxane; ethanol; H₂O / 6 h / Heating

5: 73 percent / aq. KOH / ethanol / 16 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; copper; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; water; nitrobenzene;

DOI:10.1021/jm00351a012

Reference yield:

2-iodoyl-5-methylbenzoic acid (52548-14-8) → 4-(2'-carboxymethyl-4'-methylphenoxy)phenylacetic acid (72619-35-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / K₂CO₃, Cu / nitrobenzene / 0.5 h / 140 - 150 °C

2: LiAlH₄ / tetrahydrofuran / 4 h / Heating

3: SOCl₂ / CHCl₃ / 1 h / Heating

4: dioxane; ethanol; H₂O / 6 h / Heating

5: 73 percent / aq. KOH / ethanol / 16 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; copper; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; water; nitrobenzene;

DOI:10.1021/jm00351a012

upstream raw materials:

[2-(4-Cyanomethyl-phenoxy)-5-methyl-phenyl]-acetonitrile

Ethyl 4-hydroxybenzoate

2-iodoyl-5-methylbenzoic acid

2-(4-Ethoxycarbonyl-phenoxy)-5-methyl-benzoic acid

Downstream raw materials:

8-methyl-10,11-dihydro-11-oxodibenz[b,f]oxepin-2-acetic acid