55289-06-0

Basic information

• Product Name: 3-Methoxy-2-methylbenzoic acid
• Synonyms: 3-METHOXY-O-TOLUIC ACID;3-METHOXY-2-METHYLBENZOIC ACID;2-Methyl-3-Methoxy Benzoic Acid;3-Methoxy-o-toluic acid~2-Methyl-m-anisic acid;2-Methyl-m-anisicacid;Methoxy-2-Methylbenzoic
• CAS NO: 55289-06-0
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 1533716-785-6
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;intermediate
• Mol File: 55289-06-0.mol
• Article Data: 23

Chemical Properties

• Melting Point: 147.0 to 151.0 °C
• Boiling Point: 297 °C at 760 mmHg
• Flash Point: 119.9 °C
• Appearance: /
• Density: 1.168 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.83±0.10(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• BRN: 510395
• CAS DataBase Reference: 3-Methoxy-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-2-methylbenzoic acid(55289-06-0)
• EPA Substance Registry System: 3-Methoxy-2-methylbenzoic acid(55289-06-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 55289-06-0(Hazardous Substances Data)

Usage

Description

3-Methoxy-2-methylbenzoic acid, also known as methyl gallate, is an organic compound belonging to the class of benzoic acids. It is characterized by the presence of a methoxy group at the 3rd position and a methyl group at the 2nd position on the benzene ring. 3-Methoxy-2-methylbenzoic acid exhibits various chemical properties and reactivity, making it a versatile building block in organic synthesis and a potential candidate for pharmaceutical and chemical applications.

Uses

Used in Pharmaceutical Industry:
3-Methoxy-2-methylbenzoic acid is used as a Corey-Bakshi-Shibata oxazaborolidine catalyst for asymmetric reduction and asymmetric synthesis. It plays a crucial role in the development of pharmaceutical compounds with specific stereochemistry, which is essential for their biological activity and efficacy.
Used in Chemical Synthesis:
3-Methoxy-2-methylbenzoic acid is used in the asymmetric reduction of prochiral ketones, a key step in the synthesis of various chiral compounds. This application is vital for the production of enantiomerically pure compounds, which are often required in the pharmaceutical, agrochemical, and fragrance industries.
Used in Enantioselective Synthesis:
3-Methoxy-2-methylbenzoic acid is employed in the enantioselective synthesis of α-hydroxy acids, α-amino acids, C2 symmetrical ferrocenyl diols, and propargyl alcohols. These chiral building blocks are essential for the development of new drugs, agrochemicals, and other specialty chemicals with improved selectivity and performance.
Used in Desymmetrizing Reduction:
3-Methoxy-2-methylbenzoic acid is also used in desymmetrizing reduction, leading to the production of (S)-4-hydroxycyclohexenone. This process is important for the synthesis of complex molecules with specific stereochemistry, which are often found in natural products and have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 603-80-5 3-hydroxy 2-methylbenzoic acid 
• 77-78-1 dimethyl sulfate 
• 586-38-9 3-Methoxybenzoic acid 
• 74-88-4 methyl iodide 
• 55289-05-9 methyl 3-hydroxy-2-methylbenzoate 
• 3260-88-6 1-chloro-3-methoxy-2-methylbenzene 
• 10533-44-5 trisodium 1,3,5-naphthalenetrisulfonate 
• 118-69-4 2,6-dichlorotoluene 
• 59382-59-1 2-methyl-3-nitro-benzoic acid methyl ester 
• 18583-89-6 methyl 3-amino-2-methylbenzoate 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 83-41-0 2,3-dimethylnitrobenzene 
• 95-47-6 o-xylene 
• 74-96-4 ethyl bromide 

Downstream Products

• 24487-91-0 3-methoxy-2-methylbenzoyl chloride 
• 857652-06-3 2-bromomethyl-3-methoxybenzoic acid 
• 95330-29-3 3-methoxy-2,N-dimethylbanzamide 
• 163336-50-3 N-(3-methoxy-2-methylbenzoyl)-N'-tert-butylhydrazine 
• 603-80-5 3-hydroxy 2-methylbenzoic acid 
• 161050-58-4 methoxyfenoside 
• 55289-17-3 6-bromo-3-methoxy-2-methylbenzoic acid 
• 24487-92-1 1-(3-methoxy-2-methylphenyl)ethanone 
• 1221486-03-8 R-8-(2-aminophenylamino)-1-(2,3-dihydroxypropoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one 
• 1221486-02-7 S-8-(2-aminophenylamino)-1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one 
• 1221485-99-9 8-(2-aminophenylamino)-1-methoxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one 

Relevant articles and documents

Synthesis process 2 - methyl -3 - methoxybenzoic acid

The invention discloses a synthesis process of 2 - methyl -3 - methoxybenzoic acid, which comprises the following steps: (1) reducing hydrogenation reaction: taking 2 - methyl -3 - nitrobenzoic acid or 2 - methyl -3 - nitrobenzoate as raw materials and methanol as a solvent. The hydrogen is a hydrogen source, and palladium carbon or platinum carbon is used as a catalyst to prepare 3 - amino -2 - methyl benzoic acid or 3 - amino -2 - methyl benzoic acid methyl ester by hydrogenation reduction. (2) Diazotization and hydrolysis and esterification one-pot reaction: preparing and hydroxyl 3 - methyl benzoic acid methyl ester by carrying out diazotization and hydrolysis -2 - esterification reaction under the action of a reducing product as a raw material and methanol as a solvent and a diazotization reagent. (3) Methylation reaction: methyl benzoate serving 3 - hydroxyl -2 - is used as a raw material, dimethyl sulfate is used as a methylation reagent, and methyl benzoate is produced 3 - methoxy -2 - methyl benzoate in the presence of a base. (4) Hydrolysis Reaction: methyl 3 - methoxy -2 - methyl benzoate and base. Water is mixed, heated and hydrolyzed, the reaction is complete, the product precipitated by acid conditioning PH through 1-3, filtered, and dried to obtain 3 - methoxy -2 -methylbenzoic acid.

2-methyl-3-methoxybenzoic acid and preparation method thereof

The invention belongs to the field of compound synthesis, and discloses 2-methyl-3-methoxybenzoic acid and a preparation method thereof, wherein the 2-methyl-3-methoxybenzoic acid is prepared from thefollowing raw materials: 2-methyl-3-chloroanisole, methylbenzene, tetrahydrofuran, magnesium chips, an initiator and a carboxylating agent. According to the invention, the preparation method solves the problems of large pollution hazard, high cost and low yield in the existing 2-methyl-3-methoxybenzoic acid preparation method; and the yield of the intermediate 2-methyl-3-chloroanisole of 2-methyl-3-methoxybenzoic acid obtained in the preparation method can reach 90-91%, the yield of 2-methyl-3-methoxybenzoic acid prepared from 2-methyl-3-chloroanisole is about 88%, the reaction is easy to control, the pollution is small, and the cost is low.

Synthesis method of 2-methyl-3-methoxybenzoic acid

The invention relates to a synthesis method of 2-methyl-3-methoxybenzoic acid. The preparation method comprises the specific steps: A, adding a proper amount of a sodium methoxide solution, 2,6-dichlorotoluene, dimethylformamide and a cuprous salt into a reaction kettle, stirring to rise the temperature, controlling the temperature at 80 DEG C to 150 DEG C and carrying out a reaction, to obtain 2-methyl-3- chloroanisole; and B, adding a proper amount of butyl oxide and magnesium into another reaction kettle, controlling the temperature at 30 DEG C to 60 DEG C, adding a mixed liquid of bromoethane and 2-methyl-3-chlorobenzene, carrying out a reaction for 20 min-40 min, controlling the temperature at 40 DEG C to 60 DEG C, adding 2-methyl-3- chlorobenzene drop by drop, after drop-by-drop addition is finished, carrying out a heat preservation reaction for 1.5 h-2.5 h, then cooling to -15 DEG C to -5 DEG C, adding dry ice in batches, controlling the temperature at 0 DEG C to 20 DEG C, carrying out a heat preservation reaction for 2 h to 4 h, then recycling butyl oxide, adjusting the pH value, and separating out a white powder, namely 2-methyl-3-methoxybenzoic acid. The synthesis methodof the 2-methyl-3-methoxybenzoic acid is simple in route and high in yield.