3-Methoxy-4-methylbenzoic acid

Base Information

• Chemical Name: 3-Methoxy-4-methylbenzoic acid
• CAS No.: 7151-68-0
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29189900
• European Community (EC) Number: 230-486-1
• NSC Number: 70224
• DSSTox Substance ID: DTXSID90221742
• Nikkaji Number: J125.880J
• Wikidata: Q72490350
• Mol file: 7151-68-0.mol

Synonyms:m-Anisicacid, 4-methyl- (6CI);4-Methyl-3-methoxybenzoic acid;NSC 70224;

Chemical Property of 3-Methoxy-4-methylbenzoic acid

Chemical Property:

• Appearance/Colour: slightly yellow fine powder
• Vapor Pressure: 0.000267mmHg at 25°C
• Melting Point: 152-154 °C(lit.)
• Boiling Point: 309.9 °C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 126.2 °C
• PSA: 46.53000
• Density: 1.168 g/cm³
• LogP: 1.70180
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

98%, ^*data from raw suppliers

3-Methoxy-4-methylbenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(=O)O)OC
• Uses: 3-Methoxy-4-methylbenzoic Acid is used in the preparation of acyl pentapetide lactone in actinomycin-prodcing streptoycetes.

Technology Process of 3-Methoxy-4-methylbenzoic acid

There total 8 articles about 3-Methoxy-4-methylbenzoic 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: 60.0%

3-Methoxybenzoic acid (586-38-9) + methyl iodide (74-88-4) → 3-methoxy-p-toluic acid (7151-68-0)

Guidance literature:

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 ℃; for 1.66667h;

DOI:10.1016/S0040-4039(00)00320-8

Reference yield: 9.0%

3-Methoxybenzoic acid (586-38-9) + methyl iodide (74-88-4) → 3-methoxy-p-toluic acid (7151-68-0) + 3-methoxy-2-methylbenzoic acid (55289-06-0)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; hexane; cyclohexane; 1.) -90 deg C, 60 min, 2.) -78 deg C;

DOI:10.1021/jo00094a007

Reference yield:

methyl 4-methyl-3-methoxybenzoate (3556-83-0) → 3-methoxy-p-toluic acid (7151-68-0)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

methyl 4-methyl-3-methoxybenzoate

5-bromo-2-methylphenol methyl ether

2,5-Dimethyl-anisol

3-Methoxybenzoic acid

Downstream raw materials:

3-methoxy-4-methyl-2-nitro-benzoic acid

3-Methoxy-4-{6-[3-(2-trifluoromethyl-phenyl)-ureido]-indol-1-ylmethyl}-benzoic acid methyl ester

4-(6-Hexylamino-indol-1-ylmethyl)-3-methoxy-benzoic acid

3-Methoxy-4-[6-(2-phenyl-butyrylamino)-indol-1-ylmethyl]-benzoic acid

Refernces

• 1、 Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques. "First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation". . p. 3419 - 3429. Retrieved 2008/02/03.
• 2、 Sinha, Surajit,Mandal, Bhubaneswar,Chandrasekaran, Srinivasan. "Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium-potassium tert-butoxide (LIC-KOR): Synthesis of 3,5-dimethoxy-4-methyl benzoic acid". . p. 3157 - 3160. Retrieved 2007/10/03.