143211-10-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is used as a reagent in the pharmaceutical industry for its ability to facilitate the synthesis of various medicinal compounds. Its unique structure allows for the creation of complex molecular entities that can address specific therapeutic needs.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is employed as an intermediate in the synthesis of compounds that contribute to the development of pesticides and other agricultural chemicals. Its role in this industry is crucial for enhancing crop protection and yield.
Used in Fine Chemicals Industry:
Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is utilized as a key intermediate in the production of fine chemicals, which are high-purity chemicals used in various applications such as fragrances, dyes, and specialty chemicals. Its presence in these syntheses ensures the quality and performance of the final products.
Used in Organic Synthesis:
As a reagent in organic synthesis, Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is used for its capacity to participate in a variety of organic reactions, enabling the formation of complex molecular structures. This makes it an indispensable component in the synthesis of a wide range of organic compounds.

Synthetic route

methanol (67-56-1) + 2-[(2-methylphenoxy)methyl]benzoyl cyanide (143211-11-4) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
With toluene-4-sulfonic acid In water; 1,2-dichloro-ethane at 3 - 20℃; for 5h; Temperature; Reagent/catalyst;	93%
Stage #1: 2-[(2-methylphenoxy)methyl]benzoyl cyanide With hydrogenchloride; acetic anhydride In tert-butyl methyl ether at -5 - 30℃; for 10h; Stage #2: methanol In tert-butyl methyl ether for 5h; Reflux;	85%

monomethyl oxalyl chloride (5781-53-3) + 2-(2-methylphenoxymethyl)phenylzinc chloride → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0℃; for 4h; Substitution;	61%

2-[(2-methylphenoxy)methyl]benzoyl cyanide (143211-11-4) + tert-butyl methyl ether (1634-04-4) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
With hydrogenchloride; acetic anhydride In methanol; water

2-[(2-methylphenoxy)methyl]benzoyl cyanide (143211-11-4) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
With hydrogenchloride; acetic anhydride In methanol; chloroform-d1; dichloromethane; toluene

methanol (67-56-1) + 2-[(2-methylphenoxy)methyl]benzoyl cyanide (143211-11-4) → 2-o-tolyloxymethylbenzoic acid methyl ester (143358-86-5) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Stage #1: 2-[(2-methylphenoxy)methyl]benzoyl cyanide With hydrogenchloride In 5,5-dimethyl-1,3-cyclohexadiene at -5 - 0℃; for 2h; Stage #2: methanol With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene at 15 - 65℃; for 13h;

2-[(2-methylphenoxy)methyl]benzoic acid (108475-90-7) → 2-o-tolyloxymethylbenzoic acid methyl ester (143358-86-5) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide / 8 h / 50 °C 2.1: tetrabutylammomium bromide / 5,5-dimethyl-1,3-cyclohexadiene; water / 6 h / 10 - 20 °C 3.1: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / -5 - 0 °C 3.2: 13 h / 15 - 65 °C View Scheme

2-[(2-methylphenoxy)methyl]benzoyl chloride (143211-21-6) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrabutylammomium bromide / 5,5-dimethyl-1,3-cyclohexadiene; water / 6 h / 10 - 20 °C 2.1: hydrogenchloride / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / -5 - 0 °C 2.2: 13 h / 15 - 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C 2.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C 2.2: 5 h / Reflux View Scheme

ortho-cresol (95-48-7) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 1 h / 20 °C 1.2: 2 h / 190 °C 2.1: thionyl chloride / 3 h / Reflux 3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C 4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C 4.2: 5 h / Reflux View Scheme

2-benzofuran-1(3H)-one (87-41-2) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 1 h / 20 °C 1.2: 2 h / 190 °C 2.1: thionyl chloride / 3 h / Reflux 3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C 4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C 4.2: 5 h / Reflux View Scheme

2-[(2-methylphenoxy)methyl]benzoic acid (108475-90-7) → 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 3 h / Reflux 2.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C 3.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C 3.2: 5 h / Reflux View Scheme

N-methoxylamine hydrochloride (593-56-6) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate (143390-89-0)

Conditions	Yield
In methanol for 6h; Reflux;	84.8%

N-methoxylamine hydrochloride (593-56-6) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate (143390-89-0) + methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate (248582-68-5)

Conditions	Yield
In pyridine at 20℃; for 17.5h; Condensation;	A 63% B 28%

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate (143390-89-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 28 percent / pyridine / 17.5 h / 20 °C 2: I2 / benzene / 120 h / 63 °C / UV-irradiation View Scheme

methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal (143390-88-9) + N-methoxylamine hydrochloride (593-56-6) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate (143390-89-0)

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane

hydroxylamine hydrochloride (5470-11-1) + 2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime (150869-72-0)

Conditions	Yield
With hydrogenchloride In methanol; diethyl ether

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → C16H14O4

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 45℃; for 1h;

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester (143211-10-3) → (E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid (1007364-30-8) + C17H17NO4 (1462379-39-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrabutylammomium bromide / 5,5-dimethyl-1,3-cyclohexadiene; water / 1 h / 45 °C 2: water / 1 h / 20 °C View Scheme

Upstream product

• 5781-53-3 monomethyl oxalyl chloride 
• 143211-11-4 2-[(2-methylphenoxy)methyl]benzoyl cyanide 
• 67-56-1 methanol 
• 108475-90-7 2-[(2-methylphenoxy)methyl]benzoic acid 
• 87-41-2 2-benzofuran-1(3H)-one 
• 95-48-7 ortho-cresol 
• 1634-04-4 tert-butyl methyl ether 
• 143211-21-6 2-[(2-methylphenoxy)methyl]benzoyl chloride 

Downstream Products

• 143390-89-0 methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate 
• 1007364-30-8 (E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid 
• 1462379-39-0 C₁₇H₁₇NO₄ 
• 150869-72-0 methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime 
• 248582-68-5 methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate 

Relevant academic research and scientific papers

Green synthetic method of kresoxim-methyl

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a green synthetic method of kresoxim-methyl. The method comprises the following steps: carrying out nitrous nitrification by using 2-methylbenzyl cyanide as an initial raw material, carrying out methylation, carrying out hydrolytic methylation or hydrolytic esterification, carrying out bromination and carrying out an etherification reaction to obtain the high-content kresoxim-methyl. The method provided by the invention has a short reaction period, a high conversion rate, and excellent product quality, changes the defect that high-concentration hydrochloric acid gas is used for preparation in a traditional process, and has the advantages of simple operation steps, simple equipment, low energy consumption, a short period, high productivity and environmental protection.

Synthesis method of 2-(2-methyl phenoxymethyl)-methyl benzoyl formate

The invention belongs to the technical field of fine chemical engineering, and relates to a pharmaceutical chemical synthesis technology, in particular to a synthesis method of 2-(2-methyl phenoxymethyl)-methyl benzoyl formate. The 2-(2-methyl phenoxymethyl)-methyl benzoyl formate is prepared by enabling 2-(2-methyl phenoxymethyl) benzoyl cyanide serving as a starting material react with methanolunder the action of a catalyst. The method avoids the disadvantages of use of high-concentration hydrochloric acid gas in a traditional process, so that the reaction cycle is short, the conversion rate is high, and the product quality is excellent; furthermore, the operation steps are simple, and the required equipment is simple; the method has the characteristics of low energy consumption, shortperiod, high productivity, environmental friendliness and the like.

AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL

The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.

A novel method for the efficient synthesis of methyl 2-oxo-2- arylacetates and its application to the preparation of fungicidal methyl (E)- O-methyloximino-2-arylacetates and their (Z)-stereoisomers

Methyl 2-oxo-2-arylacetates 1, which include some fluorinated compounds, have been synthesized in moderate to excellent yields by reaction of methyl oxalyl chloride with arylzinc halides in the presence of Pd(PPh3)4. The highest yields have been obtained when these reactions involved arylzinc bromides which were prepared by conversion of the corresponding aryl bromides to organolithiums, followed by transmetallation with ZnBr2. Compounds 1 have been converted in high yields to the corresponding (E)- and (Z)-O- methyloximino-2-arylacetates (E)- and (Z)-5 by treatment with O- methylhydroxylamine hydrochloride in pyridine. Compounds (E)- and (Z)-5 have been easily separated by MPLC on silica gel and their structure and stereochemistry have been assigned by NMR techniques. So prepared compounds of general formula 5 included an agrochemically important fungicide, i.e. (E)-5c, its fluorinated structural analogues, as well as compounds which proved to be able to delay the growth of fungal species isolated from deteriorated papers. Interestingly, several compounds of general formula (Z)- 5 underwent partial stereomutation in the presence of daylight and catalytic amounts of iodine.

Preparation of E-oxime ethers of phenylglyoxylic esters

E-oxime ethers of phenylglyoxylic esters of the formula I STR1 where X and Y are each halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or trifluoromethyl; m is an integer from 0 to 4; n is an integer from 0 to 3; are prepared.