Ethyl 4-methoxy-3,5-dimethylbenzoate

Base Information

• Chemical Name: Ethyl 4-methoxy-3,5-dimethylbenzoate
• CAS No.: 105401-94-3
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID001347928
• Nikkaji Number: J354.728K
• Wikidata: Q63395481
• Mol file: 105401-94-3.mol

Synonyms:ETHYL 4-METHOXY-3,5-DIMETHYLBENZOATE;105401-94-3;4-Methoxy-3,5-dimethylbenzoic acid ethyl ester;Benzoic acid, 4-methoxy-3,5-dimethyl-, ethyl ester;starbld0024017;SCHEMBL8985829;VTPOFWHQBYJVTQ-UHFFFAOYSA-N;DTXSID001347928;MFCD11555029;Ethyl 3,5-dimethyl-4-methoxybenzoate;CS-0189058;3,5-Dimethyl-4-methoxybenzoic acid ethyl ester;E90524;4-Methoxy-3,5-dimethyl-benzoic acid ethyl ester;Q63395481

Chemical Property of Ethyl 4-methoxy-3,5-dimethylbenzoate

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy-3,5-dimethylbenzoicacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl 4-methoxy-3,5-dimethylbenzoate

There total 8 articles about Ethyl 4-methoxy-3,5-dimethylbenzoate 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: 44.0%

ethyl 3-iodo-4-methoxybenzoate (207115-38-6) + carbonic acid dimethyl ester (616-38-6) → ethyl 4-methoxy-3,5-dimethylbenzoate (105401-94-3) + C12H15(2)HO3

Guidance literature:

ethyl 3-iodo-4-methoxybenzoate; With tetrabutylammomium bromide; potassium carbonate; palladium dichloride; In N,N-dimethyl acetamide; Schlenk technique; Inert atmosphere;

carbonic acid dimethyl ester; With d⁽⁴⁾-methanol; In N,N-dimethyl acetamide; at 105 ℃; for 12h; Reagent/catalyst; Overall yield = 29 mg; regioselective reaction; Mechanism; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.0c13057

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → ethyl 4-methoxy-3,5-dimethylbenzoate (105401-94-3) + ethyl 7-methyl-2,3-dihydrobenzofuran-5-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine; ammonium hydroxide / methanol / 3 h / 20 °C

2.1: sulfuric acid / 8 h / 100 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: tetrabutylammomium bromide; palladium diacetate; potassium acetate / N,N-dimethyl acetamide / Schlenk technique; Inert atmosphere

4.2: 12 h / 105 °C / Schlenk technique; Inert atmosphere

With ammonium hydroxide; sulfuric acid; tetrabutylammomium bromide; iodine; potassium acetate; palladium diacetate; potassium carbonate; In methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jacs.0c13057

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → ethyl 4-methoxy-3,5-dimethylbenzoate (105401-94-3) + C12H15(2)HO3

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine; ammonium hydroxide / methanol / 3 h / 20 °C

2.1: sulfuric acid / 8 h / 100 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C

4.1: palladium dichloride; tetrabutylammomium bromide; potassium carbonate / N,N-dimethyl acetamide / Schlenk technique; Inert atmosphere

4.2: 12 h / 105 °C / Schlenk technique; Inert atmosphere

With ammonium hydroxide; sulfuric acid; tetrabutylammomium bromide; iodine; potassium carbonate; palladium dichloride; In methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/jacs.0c13057

upstream raw materials:

ethyl 3-iodo-4-methoxybenzoate

carbonic acid dimethyl ester

4-hydroxy-benzoic acid

4-hydroxy-3-iodobenzoic acid

Refernces