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

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

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

• 31804-36-1 1-bromo-3-methoxy-2-methylbenzene 
• 42981-93-1 3-methoxy-2-methylbenzoic acid methyl ester 
• 77533-17-6 3-methoxy-2-methylbenzonitrile 
• 57598-32-0 4,5-dihydro-2-(2',3'-dimethoxyphenyl)-4,4-dimethyloxazole 
• 75-16-1 methylmagnesium bromide 
• 72623-17-7 2-(2-Methyl-3-methoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 109789-23-3 (2R,6R)-2-(3-Methoxy-2-methyl-phenyl)-4,4,6-trimethyl-[1,3]dioxane 
• 586-38-9 3-Methoxybenzoic acid 
• 74-88-4 methyl iodide 
• 3260-88-6 1-chloro-3-methoxy-2-methylbenzene 
• 124-38-9 carbon dioxide 
• 73453-77-7 3-(4,4-dimethyloxazolin 2-yl)anisole 
• 131-27-1 3-amino-1,5-naphthalenedisulfonic acid 
• 83-42-1 6-chloro-2-nitrotoluene 

Downstream Products

• 24487-91-0 3-methoxy-2-methylbenzoyl chloride 
• 33797-34-1 (3-methoxy-2-methylphenyl)methanol 
• 627883-78-7 3-methoxy-2-methyl-benzoic acid ethyl ester 
• 857652-06-3 2-bromomethyl-3-methoxybenzoic acid 
• 135329-22-5 3-methoxy-2-methylbenzamide 
• 95330-29-3 3-methoxy-2,N-dimethylbanzamide 
• 857651-74-2 2-bromomethyl-3-methoxy-benzaldehyde 
• 857652-07-4 (2-bromomethyl-3-methoxy-phenyl)-methanol 
• 627883-79-8 2-(bromomethyl)-3-methoxybenzoic acid ethyl ester 
• 176088-64-5 3-Methoxy-2-methyl-N-((1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-benzamide 
• 149653-77-0 (S)-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-methoxy-2-methylbenzamide 
• 117498-59-6 (3-Methoxy-2-methyl-phenyl)-thiophen-2-yl-methanone 
• 117498-65-4 (3,4-Diamino-2-methyl-phenyl)-thiophen-2-yl-methanone 
• 117498-64-3 (3-Amino-2-methyl-4-nitro-phenyl)-thiophen-2-yl-methanone 

Relevant articles and documents

Preparation method of 6-chloro-2-methoxytoluene and synthesis process of methoxyfenozide

The invention relates to the field of insecticides, in particular to a preparation method of 6-chloro-2-methoxytoluene and a synthesis process of methoxyfenozide. The preparation method of the 6-chloro-2-methoxytoluene comprises the following steps: in a solvent, mixing 2, 6-dichlorotoluene with sodium methoxide, and carrying out a substitution reaction to prepare a first reaction solution containing 3-chloro-2-sodium methylphenolate and the 6-chloro-2-methoxytoluene; and dropwise adding dimethyl sulfate into the first reaction solution, carrying out etherification reaction, removing 3-chloro-2-sodium methylphenolate to obtain a second reaction solution, and carrying out post-treatment to obtain the 6-chloro-2-methoxytoluene. The synthesis process of the methoxyfenozide comprises the following steps: preparing 3-methoxy-2-methyl benzoic acid by taking 6-chloro-2-methoxytoluene as an intermediate; using 3-methoxy-2-methyl benzoic acid and 3, 5-dimethyl benzoic acid as intermediates, and preparing to obtain the methoxyfenozide. According to the synthesis process disclosed by the invention, the yield and the purity of methoxyfenozide can be remarkably improved.

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.

2-methyl-3-methoxybenzoyl chloride synthesizing process

The invention discloses a 2-methyl-3-methoxybenzoyl chloride synthesizing process. According to the present invention, low-cost o-xylene is used as a starting raw material, the product is synthesizedby using a conventional synthesis method comprising nitrification, esterification, reduction, diazotization, methylation, acyl chlorination and other steps, and the total yield is controlled at more than 65%; the esterification of the intermediate product improves the separation degree of the intermediate; the reaction solvent is added in the diazotization step, such that the process parameters are relatively easy to control, and the purity of the intermediate in the diazotization step is more than 96% so as to provide the guarantee for the quality of the subsequent product; and with the synthesis process, the product quality is stable and reliable, 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.

Preparation method of 2-methyl-3-methoxybenzoic acid

The invention relates to a preparation method of 2-methyl-3-methoxybenzoic acid. The preparation method comprises the following specific steps: A, adding a proper amount of a sodium methoxide solution, 2,6-dichlorotoluene, dimethylformamide and cuprous salt into a reaction kettle; stirring and raising the temperature; controlling the temperature to 80 DEG C to 150 DEG C and reacting to obtain 2-methyl-3-chloroanisole; B, adding a proper amount of tetrahydrofuran and magnesium into the other reaction kettle; controlling the temperature to be 30 DEG C to 60 DEG C; adding a mixed solution of bromoethane and the 2-methyl-3-chloroanisole; after reacting for 20min to 40min, controlling the temperature to be 40 DEG C to 60 DEG C and dropwise adding the 2-methyl-3-chloroanisole; after dropwise adding, keeping heat and reacting for 1.5h to 2.5h; then cooling to -15 DEG C to -5 DEG C; adding dry ice by batches; controlling the temperature to be 0 DEG C to 20 DEG C, keeping the heat and reactingfor 2h to 4h; then recycling the tetrahydrofuran; adjusting the pH (Potential of Hydrogen) value to separate out white powder, namely the 2-methyl-3-methoxybenzoic acid. The preparation method of the2-methyl-3-methoxybenzoic acid, provided by the invention, is simple in route and high in yield.

Preparation method for 2-methyl-3-methoxybenzoic acid and preparation method for intermediate thereof

The invention discloses a preparation method for 2-methyl-3-methoxybenzoic acid and a preparation method for an intermediate thereof. The preparation method for the intermediate namely 2-methyl-3-chlorobenzoic acid comprises the following steps: introducing oxygen into a mixed solution of a C2-6 organic acid, a catalyst and 3-chloro-ortho-xylene, and carrying out a reaction, wherein the catalyst is a cobalt-manganese-bromine composite catalyst or a cobalt-bromine composite catalyst; the reaction temperature is 100 to 210 DEG C; the reaction pressure is 0.1 to 3 MPa; and the introduction time of the oxygen is 1 to 12 h. The preparation method provided by the invention uses 3-chloro-ortho-xylene as a starting material, has the advantages of simple and convenient process, short production period, high yield, clean production and reduced cost, and is applicable to industrial production.

First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation

(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).

Toward a better understanding on the mechanism of ortholithiation. Tuning of selectivities in the metalation of meta-anisic acid by an appropriate choice of base

(Chemical Equation Presented) If employed in THF at 0°C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand. As a result of these findings, a new mechanism is proposed for the heteroatom-directed ortholithiation of aromatic compounds.

Preparation of 3-alkoxy-2-methylbenzoic acids

The invention relates to an improved process for preparing 3-alkoxy-2-methylbenzoic acids by heating substituted naphthalenes in the presence of alkali metal hydroxides and subsequently alkylating.