143211-10-3

Basic information

• Product Name: Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate
• Synonyms: Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate;Methyl 2-oxo-2-(2-(o-tolyloxymethyl)phenyl)acetate;methyl 2-[2-[(2-methylphenoxy)methyl]phenyl]-2-oxoacetate
• CAS NO: 143211-10-3
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.30654
• EINECS: 2-(2-甲基苯基氧甲基)苯基草酸草酯
• Mol File: 143211-10-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 53-55℃
• Boiling Point: 425.436 °C at 760 mmHg
• Flash Point: 188.131 °C
• Appearance: /
• Density: 1.175 g/cm³
• CAS DataBase Reference: Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate(143211-10-3)
• EPA Substance Registry System: Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate(143211-10-3)

Safety Data

• Hazardous Substances Data: 143211-10-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is a compound with the chemical formula C18H18O4. It is a yellow crystalline solid that is commonly used as a reagent in organic synthesis. Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is often utilized in the production of pharmaceuticals, agrochemicals, and fine chemicals. It is also employed as an intermediate in the synthesis of various organic compounds. Methyl 2-(2-methylphenoxymethyl)phenylglyoxylate is known for its role in organic reactions, particularly as a key component in the construction of complex molecular structures.

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

Downstream Products

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

Relevant articles and documents

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

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Preparation of E-oxime ethers of phenylglyoxylic esters

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