34046-43-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Formylbenzoic acid ethyl ester is used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its chemical properties allow it to be a key component in the development of new drugs and medications.
Used in Flavoring Agent Applications:
In the food industry, 2-Formylbenzoic acid ethyl ester is used as a flavoring agent. Its unique properties contribute to the taste and aroma of various food products, enhancing the overall sensory experience for consumers.
Used in Organic Chemistry:
2-Formylbenzoic acid ethyl ester is used as an important reagent in organic chemistry, particularly in the production of esters, aldehydes, and carboxylic acids. Its versatility and stability make it a valuable component in various chemical reactions and processes.

InChI:InChI=1/C10H10O3/c1-2-13-10(12)9-6-4-3-5-8(9)7-11/h3-7H,2H2,1H3

Synthetic route

ethyl iodide (75-03-6) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	98%
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	79%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	68%

ethanol (64-17-5) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 12h;	85%

ethanol (64-17-5) + o-phthalic dicarboxaldehyde (643-79-8) → 3-ethoxy-3H-isobenzofuran-1-one (16824-02-5) + ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate at 60℃;	A 78% B 8%

ethyl 2-(2-hydroxybenzylidine)-hydrazine carboxylate (88674-90-2) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane for 2h; Ambient temperature;	72%
With lead(IV) acetate In tetrahydrofuran for 2h; Ambient temperature;	60%

ethyl cyclohepta-2,4,6-trienecarboxylate (27332-37-2) → ethyl 2-formylbenzoate (34046-43-0) + (1R,2S,3R,4R,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carboxylic acid ethyl ester + C10H12O4

Conditions	Yield
With hematoporphyrin In acetone Irradiation;	A 6% B 70% C 8%

ethyl 2-methylbenzoate (87-24-1) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dipotassium peroxodisulfate; cobalt(II) diacetate tetrahydrate; trifluoroacetic acid; trifluoroacetic anhydride at 80℃; chemoselective reaction;	69%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + ethanol (64-17-5) + ortho-bromobenzaldehyde (6630-33-7) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 0.5h; Microwave irradiation;	65%

triethyloxonium fluoroborate (368-39-8) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With triethylamine In dichloromethane for 2h; Ambient temperature;	60%

ethyl cyclohepta-2,4,6-trienecarboxylate (27332-37-2) → ethyl 2-formylbenzoate (34046-43-0) + benzoic acid ethyl ester (93-89-0) + p-ethoxycarbonylbenzaldehyde (6287-86-1) + Ethyl 2-phenylethanoate (101-97-3) + Diethyl maleate (141-05-9)

Conditions	Yield
With sodium acetate; palladium diacetate In acetic acid at 80℃; for 4h; Product distribution; Mechanism; also 7-cyano-1,3,5-cycloheptatriene, var. solvents and reaction conditions;	A 11 % Spectr. B 8% C 9 % Spectr. D 3% E 4%

o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With thionyl chloride Behandeln des Reaktionsprodukts mit Alkohol;

(2-Ethoxycarbonyl-phenylmethylidyne)-isopropyl-ammonium → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With triethylsilane; water 1) CH2Cl2, reflux, 2) heating; Yield given. Multistep reaction;

4-Ethoxy-1,4-dihydro-2,3-benzodioxin-1-ol (70760-53-1) → ethyl 2-formylbenzoate (34046-43-0) + o-carboxybenzaldehyde (119-67-5)

Conditions	Yield
With water In acetonitrile at 29.6℃; Rate constant; Mechanism; variation of water-content, other solvents without water; addition of dimethylpyrroline N-oxide (formation of OH* adduct), also with D2O;

diethyl sulfate (64-67-5) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With potassium hydroxide; Aliquat 336 1.) 60 deg C, 0.1 Torr, 6 h, 2.) room temp., 18 h; Yield given. Multistep reaction;
With potassium hydroxide; Aliquat 336
With triethylamine In dichloromethane

2-cyano-benzoic acid ethyl ester (6525-45-7) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: FeCl3 / CH2Cl2 / Heating 2: 1) Et3SiH, 2) H2O / 1) CH2Cl2, reflux, 2) heating View Scheme

ethyl 2-formylbenzoate (34046-43-0) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) → ethyl 2-(oxazol-5-yl)benzoate (1186127-15-0)

Conditions	Yield
With triethylamine; β‐cyclodextrin In water at 50℃; for 2h; Green chemistry;	94%

ethyl 2-formylbenzoate (34046-43-0) + allyl bromide (106-95-6) → 3-allyl-3H-isobenzofuran-1-one (24282-29-9, 148761-98-2)

Conditions	Yield
With tin In tetrahydrofuran at 80℃; for 8h;	94%

ethyl 2-formylbenzoate (34046-43-0) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S)-ethyl 2-(((tert-butylsulfinyl)imino)methyl) benzoate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 8h;	90%

ethyl 2-formylbenzoate (34046-43-0) + allyl bromide (106-95-6) → (S)-3-allylisobenzofuran-1(3H)-one (24282-29-9)

Conditions

Yield

Stage #1: ethyl 2-formylbenzoate; allyl bromide With chromium chloride; manganese; chloro-trimethyl-silane; (10,10-dimethyl-5-(pyridin-2-yl)-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-yl)diphenylmethanol; triethylamine In tetrahydrofuran at 0℃; for 48h; Nozaki-Hiyama-Kishi Reaction; Molecular sieve; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran Molecular sieve; Inert atmosphere; Stage #3: With toluene-4-sulfonic acid In tetrahydrofuran Molecular sieve; Inert atmosphere; enantioselective reaction;

86%

ethyl 2-formylbenzoate (34046-43-0) + triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (56013-01-5) → 2-[(E)-2-(2,6,6-Trimethyl-cyclohex-1-enyl)-vinyl]-benzoic acid ethyl ester (223742-36-7)

Conditions	Yield
With n-butyllithium at 0℃;	85%

ethyl 2-formylbenzoate (34046-43-0) + malonic acid (141-82-2) → 3-(2-ethoxycarbonylphenyl)acrylic acid (188545-22-4)

Conditions	Yield
With piperidine; pyridine for 2h; Reflux;	82%

ethyl 2-formylbenzoate (34046-43-0) + (trifluoromethyl)trimethylsilane (81290-20-2) → 3-(trifluoromethyl)-1(3H)-isobenzofuranone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Concentration; Solvent;	82%

ethyl 2-formylbenzoate (34046-43-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;	81%

2-(2-methyl-1,3-dioxolane-2-yl)ethan-1-amine (62240-37-3) + ethyl 2-formylbenzoate (34046-43-0) → 1',3',4',10b'-tetrahydro-6'H-spiro[1,3-dioxolane-2,2'-pyrido[2,1-a]isoindol]-6'-one (817554-52-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Dean-Stark apparatus; Reflux;	77%

ethyl 2-formylbenzoate (34046-43-0) + 2,4-difluorophenylamine (367-25-9) → 2-(2,4-difluorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (1375015-42-1)

Conditions	Yield
Stage #1: 2,4-difluorophenylamine With TurboGrignard In tetrahydrofuran at 20℃; for 0.1h; Microreactor; Stage #2: ethyl 2-formylbenzoate In tetrahydrofuran at 20℃; for 0.233333h; Bodroux reaction; Microreactor;	70%

ethyl 2-formylbenzoate (34046-43-0) + (2-nitrobenzyl)triphenylphosphonium bromide (23308-83-0) → ethyl 2-(2-nitrostyryl)benzoate (90011-52-2)

Conditions	Yield
With sodium ethanolate In dichloromethane at 20℃; Wittig reaction;	60%

ethyl 2-formylbenzoate (34046-43-0) + allyltrimethoxysilane (2551-83-9) → (R)-3-allylisobenzofuran-1(3H)-one + (S)-3-allylisobenzofuran-1(3H)-one (24282-29-9)

Conditions	Yield
With silver fluoride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In methanol at -20℃; for 5h; Sakurai-Hosomi Allylation; enantioselective reaction;	A 58% B n/a

ethyl 2-formylbenzoate (34046-43-0) + 2-(2-(2-bromo-5-chlorophenyl)-1-iminoethyl)-5-chlorophenol → ethyl 2-(4-(2-bromo-5-chlorobenzyl)-7-chloro-2H-benzo-[e][1,3]oxazin-2-yl)benzoate

Conditions	Yield
With trifluorormethanesulfonic acid; C17H17NO3 In 2-methyltetrahydrofuran at 0 - 20℃; for 18h; Molecular sieve;	57%
Stage #1: ethyl 2-formylbenzoate; 2-(2-(2-bromo-5-chlorophenyl)-1-iminoethyl)-5-chlorophenol With C17H17NO3 In 2-methyltetrahydrofuran at 0 - 5℃; for 0.0333333h; Inert atmosphere; Molecular sieve; Stage #2: With trifluorormethanesulfonic acid In 2-methyltetrahydrofuran at 20℃; Inert atmosphere;	56.9%

ethyl 2-formylbenzoate (34046-43-0) + 4-(2-chlorophenyl)-2-hydrazinothiazole → (E)-4-(2-chlorophenyl)-2-(2-ethoxyformylbenzylidenehydrazino)thiazole

Conditions	Yield
In ethanol for 4h; Inert atmosphere;	57%

ethyl 2-formylbenzoate (34046-43-0) + 1-bromo-2-(2-chloro-ethyl)benzene (75534-18-8) → 3-[2-(2-chloroethyl)phenyl]-3H-isobenzofuran-1-one

Conditions	Yield
Stage #1: 1-bromo-2-(2-chloro-ethyl)benzene With n-butyllithium In tetrahydrofuran at -100℃; for 0.166667h; Stage #2: With ytterbium(III) triflate In tetrahydrofuran at -78℃; for 0.5h; Stage #3: ethyl 2-formylbenzoate In tetrahydrofuran at -78 - 20℃; Further stages.;	56%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + ethyl 2-formylbenzoate (34046-43-0) + N-phenacylpyridinium bromide (16883-69-5) → ethyl trans-2-(2-benzoyl-4-oxo-2,3-dihydro-4H-furo[3,2-c]chromen-3-yl)benzoate

Conditions	Yield
With triethylamine In ethanol; water for 3h; Reflux; diastereoselective reaction;	50%

Upstream product

• 119-67-5 o-carboxybenzaldehyde 
• 75-03-6 ethyl iodide 
• 27332-37-2 ethyl cyclohepta-2,4,6-trienecarboxylate 
• 88674-90-2 ethyl 2-(2-hydroxybenzylidine)-hydrazine carboxylate 
• 70760-53-1 4-Ethoxy-1,4-dihydro-2,3-benzodioxin-1-ol 
• 64-67-5 diethyl sulfate 
• 368-39-8 triethyloxonium fluoroborate 
• 6525-45-7 2-cyano-benzoic acid ethyl ester 
• 64-17-5 ethanol 
• 15226-74-1 dicobalt octacarbonyl 
• 6630-33-7 ortho-bromobenzaldehyde 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 87-24-1 ethyl 2-methylbenzoate 

Downstream Products

• 83465-27-4 (3-oxo-1,3-dihydro-isobenzofuran-1-yl)acetic acid ethyl ester 
• 142671-81-6 ethyl 2-(1,3-dithian-2-yl)benzoate 
• 136391-65-6 diazomethane 
• 223742-36-7 2-[(E)-2-(2,6,6-Trimethyl-cyclohex-1-enyl)-vinyl]-benzoic acid ethyl ester 
• 377774-83-9 2-((1E,3Z)-8-Hydroxy-octa-1,3-dienyl)-benzoic acid 
• 377774-82-8 2-((E)-8-Hydroxy-oct-1-en-3-ynyl)-benzoic acid 
• 377774-81-7 2-((1E,3Z)-8-Hydroxy-octa-1,3-dienyl)-benzoic acid ethyl ester 
• 377774-80-6 2-((E)-8-Hydroxy-oct-1-en-3-ynyl)-benzoic acid ethyl ester 
• 87-41-2 2-benzofuran-1(3H)-one 
• 90011-52-2 ethyl 2-(2-nitrostyryl)benzoate 
• 16824-02-5 3-ethoxy-3H-isobenzofuran-1-one 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 1375015-42-1 2-(2,4-difluorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one 
• 188545-22-4 3-(2-ethoxycarbonylphenyl)acrylic acid 

Relevant academic research and scientific papers

Cobalt(ii)-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA

A cobalt-catalyzed C(sp3)-H oxygenation reaction to furnish aldehyde was herein reported. This transformation demonstrated high chemo-selectivity, and tolerated various methylarenes bearing electron-withdrawing substituents. This reaction provided rapid access to diverse aldehydes form methylarenes. Notably, TFA/TFAA was used for the first time as a mixed solvent in cobalt-catalyzed oxygenation of benzylic methylenes.

THIAZOLE DERIVATIVE AND APPLICATIONS

A thiazole derivative serving as a DHODH inhibitor, and applications thereof. The present invention specifically relates to a compound represented by formula I, a pharmaceutical composition containing the compound represented by formula (I), and applications of the compound in the preparation of drugs for treating diseases mediated by the DHODH or drugs for inhibiting the DHODH.

Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds

The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.

6,5-BICYCLIC OCTAHYDROPYRROLOPYRIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to 6,5-bicyclic octahydropyrrolopyridine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

METHYL OXAZOLE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to methyl oxazole compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

ETHYLDIAMINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to ethyldiamne compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

BRIDGED DIAZEPANE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to bridged diazepane compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.

Oxidative cyclization of dialdehydes with alcohols and 1,3-dicarbonyl compounds under Rh(III)/Cu(II) conditions

For the preparation of 3-alkoxyphthalides from phthalaldehydes and alcohols, a cyclization reaction in the presence of a rhodium(III) catalyst and copper(II) salt is reported. Cyclization of phthalaldehydes also occurs with 1,3-dicarbonyl compounds under similar conditions to produce 3-substituted phthalides in good yields. An acylrhodium(III) species might be a key intermediate in these cyclization reactions.

CINNAMIC ACID AMIDE DERIVATIVE

The present invention provides a cinnamic acid amide derivative having an excellent analgesic action. The cinnamic acid amide derivative of the present invention is a compound showing excellent analgesic actions to not only a nociceptive pain model animal but also a neuropathic pain model animal, which is very useful as an agent for treating various pain diseases showing acute or chronic pains or neuropathic pains.

A synthetic route to chiral C(3)-functionalized phthalides via a Ag(I)-catalyzed allylation/transesterification sequence

A Ag(I)-catalyzed synthesis of chiral C(3)-substituted phthalides (8a-f) via a Sakurai-Hosomi allylation/transesterification reaction is described (ee ≤86%). A notable feature of this reaction is that it utilizes ortho-substituted aldehydes, which are a class of compounds that generally afford poor levels of stereoinduction when applying most known catalytic asymmetric allylation approaches. It was also found that elongation of the n-alkyl chain length (R1, up to n=6; R2=H) of the starting alkyl 2-formylbenzoates (7g-i) improved the enantiomeric excess (ee) of the product.