553-86-6

Basic information

• Product Name: 2-COUMARANONE
• Synonyms: 1-Benzofuran-2(3H)-one;2-Coumaronone;2-Cumaranon;BENZOFURAN-2-ONE;BENZOFURANONE;ISOCOUMARANONE;2H-BENZOFURANONE;2-COUMARANONE
• CAS NO: 553-86-6
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• EINECS: 209-052-0
• Product Categories: Benzofurans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 553-86-6.mol
• Article Data: 65

Chemical Properties

• Melting Point: 49-51 °C(lit.)
• Boiling Point: 248-250 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow-orange/Crystalline Powder or Crystals
• Density: 1,22 g/cm3
• Vapor Pressure: 0.0235mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: H2O: soluble3.8g/L at 30°C
• BRN: 114689
• CAS DataBase Reference: 2-COUMARANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-COUMARANONE(553-86-6)
• EPA Substance Registry System: 2-COUMARANONE(553-86-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-43-36/38
• Safety Statements: 24/25-36-26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 553-86-6(Hazardous Substances Data)

Usage

Description

2-Coumaranone (also named as Isophthalide, 3H-benzofuran-2-one) belongs to a class of organic compounds named as benzofuranones which exhibits mutagenic and carcinogenic activity. 2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland and as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.

Reference

Y. S. Priya, K. Ramachandra Rao, P. V. Chalapathi, M. Satyavani, A. Veeraiah, Vibrational and UV spectroscopic studies of 2-coumaranone by experimental and density functional theory calculations, Journal of Molecular Structure, 2017, vol. 1144, pp. 535-544

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

Uses

2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland. It was employed as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 2491, 1982 DOI: 10.1021/jo00133a055

InChI:InChI=1/C8H6O2/c9-8-5-6-3-1-2-4-7(6)10-8/h1-4H,5H2

Synthetic route

2-Hydroxyphenylacetic acid (614-75-5) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With pyrophosphoryl chloride at 35℃; for 0.333333h;	100%
With toluene-4-sulfonic acid In toluene for 4h; Heating;	100%
With sulfuric acid In water; toluene at 100℃; for 6h; Reagent/catalyst; Temperature;	98%

butyl o-acetoxyphenylacetate → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With tin(IV) oxide at 140℃; for 5h; Inert atmosphere;	98%

2-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-N,N-diethyl-acetamide → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With trifluoroacetic acid In toluene for 1h; Heating;	97%

potassium benzo[d][1,3]dioxol-5-yltrifluoroborate → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With Oxone In water; acetone at 20℃; for 0.0333333h; Cooling with ice;	97%
With Oxone; water In acetone at 20℃; for 0.0833333h;	9%
With oxone In water; acetone for 2h;	14 mg

ethyl o-acetoxyphenylacetate → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With magnesium oxide at 120℃; for 2h; Temperature; Reagent/catalyst;	97%

methyl o-acetoxyphenylacetate → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With alumina molecular sieve at 90℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;	96%

N,N-diethyl-2-(2-hydroxy)phenyl acetamide (182962-47-6) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With hydrogenchloride In toluene for 40h; Heating;	94%
With hydrogenchloride In water; benzene for 40h; Reagent/catalyst; Reflux;

2-benzofuranylboronic acid mida ester (1104637-65-1) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
Stage #1: 2-benzofuranylboronic acid mida ester With potassium hydrogen bifluoride In methanol; water at 70℃; for 2h; Stage #2: With Oxone In methanol; water at 18℃; for 0.166667h;	89%
Multi-step reaction with 2 steps 1: methanol; water / 4 h / 70 °C 2: oxone / water; acetone / 2 h View Scheme

allyl phenyl ether (1746-13-0) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
Stage #1: allyl phenyl ether With water; ozone at 15℃; Stage #2: In water at 60℃;	85%

formic acid (64-18-6) + salicylic alcohol (90-01-7) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); acetic anhydride; tris-(o-tolyl)phosphine In toluene at 30 - 100℃; for 3.5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;	84%

phenyl chloroacetate (620-73-5) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With aluminum (III) chloride In tetrachloromethane at 20℃; for 6h; Solvent; Reagent/catalyst; Temperature;	83%

5-(tert-butyl)benzofuran-2(3H)-one (24431-30-9) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With aluminum (III) chloride In toluene Reflux;	82.1%

phenoxyacetylene (4279-76-9) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With 2,6-lutidine N-oxide; tetrafluoroboric acid diethyl ether In 1,4-dioxane at 80℃; for 5h;	81%
With 2,6-lutidine N-oxide; tetrafluoroboric acid diethyl ether In 1,4-dioxane at 80℃; for 3h;	81%

phthalyl alcohol (612-14-6) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With [RuH(η2-BH4)(2-di-tert-butylphosphinomethyl-6-diethylaminomethylpyridine)] In toluene at 115℃; for 48h; Inert atmosphere;	76%
With phosphoric acid tributyl ester at 119.84℃; under 9375.94 Torr; for 8h; Catalytic behavior; Autoclave;	48%

benzofuran-2-boronic acid (98437-24-2) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With N,N-dimethyl-p-toluidine N-oxide In dichloromethane at 20℃; for 2h;	74%

methyl (2-hydroxyphenyl)acetate (22446-37-3) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With aluminum (III) chloride; 2,6-di-tert-butyl-4-methyl-phenol; trifluoroacetic acid In 1,2-dichloro-benzene at 150℃; for 4h; Inert atmosphere; Sealed tube;	70%
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen / ethanol / 20 °C / Inert atmosphere 5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen / ethanol / 20 °C / Inert atmosphere 5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen / ethanol / 20 °C / Inert atmosphere 5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 80 °C / Inert atmosphere View Scheme

2,3-Dihydrobenzofuran (496-16-2) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane at 70℃; for 24h;	69%

3-hydroxy-2-pyrone (496-64-0) + methyl 3-nitrobut-3-enoate (34805-49-7) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With aluminum (III) chloride; 2,6-di-tert-butyl-4-methyl-phenol; trifluoroacetic acid In 1,2-dichloro-benzene at 120℃; for 20h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; regioselective reaction;	64%

benzocyclobutenone (3469-06-5) → 2-benzofuran-1(3H)-one (87-41-2) + benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With Calcium tetrakis(pentafluorophenyl)borate; dihydrogen peroxide; oxalic acid In water; 1,2-dichloro-ethane at 50℃; for 6h; Reagent/catalyst;	A 63% B 24%

C20H26O8 → benzofuran-2(3H)-one (553-86-6) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9)

Conditions	Yield
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 80℃; Inert atmosphere;	A n/a B 63%

carbon monoxide (201230-82-2) + salicylic alcohol (90-01-7) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); benzoic acid In benzene at 125℃; under 3800 Torr; for 20h;	59%

carbon monoxide (201230-82-2) + salicylic alcohol (90-01-7) → benzofuran-2(3H)-one (553-86-6) + ortho-cresol (95-48-7) + 2-Hydroxyphenylacetic acid (614-75-5)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 9% B 7% C 56%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In 1,4-dioxane at 120℃; under 68400 Torr; for 42h;	A 9 % Spectr. B 7 % Spectr. C 36%

C12H19N2O4P (133642-10-1) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With formic acid for 1h; Heating;	54%

N,N-diethyl-2-methylcarbamoyloxybenzene (85630-35-9) → benzofuran-2(3H)-one (553-86-6) + N,N-diethyl-2-(2-hydroxy)phenyl acetamide (182962-47-6)

Conditions	Yield
With ammonium chloride; lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;	A 15% B 54%

3-hydroxy-2-pyrone (496-64-0) + methyl 3-nitrobut-3-enoate (34805-49-7) → benzofuran-2(3H)-one (553-86-6) + methyl (2-hydroxyphenyl)acetate (22446-37-3)

Conditions	Yield
With aluminum (III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In 1,2-dichloro-benzene at 120℃; for 2h; Inert atmosphere;	A 15% B 53%
With 2,6-di-tert-butyl-4-methyl-phenol; dimethylaluminum chloride; trifluoroacetic acid In 1,2-dichloro-benzene at 100℃; for 2.5h; Inert atmosphere;	A 30% B 29%

2-diazo-1-phenylethan-1-one (21119-50-6) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
dirhodium tetraacetate In dichloromethane for 24h;	43%

1H-benzo[4,5]furo[3,2-d]thiazol-2-ylideneamine (662109-78-6) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With sodium hydroxide In water at 20℃;	40%

4-Chlorophenoxyacetic acid (122-88-3) → benzofuran-2(3H)-one (553-86-6) + 5-chloro-2,3-dihydro-2-benzofuranone (28033-47-8) + 4-chloro-phenol (106-48-9) + 2-phenoxyacetic acid (122-59-8) + phenol (108-95-2)

Conditions	Yield
With air In water for 7h; Product distribution; Ambient temperature; Irradiation; also under argon atmosphere; photodegradation pathways;	A 7% B 12% C 28% D 3% E 38%

2-allylphenol (695-84-1) → benzofuran-2(3H)-one (553-86-6)

Conditions	Yield
With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; water; copper dichloride; palladium dichloride In nitromethane at 80℃; for 24h; chemoselective reaction;	35%

1-benzofurane (271-89-6) → benzofuran-2(3H)-one (553-86-6) + 2-hydroxy-3(2H)-benzofuranone (17392-15-3) + salicylaldehyde (90-02-8)

Conditions	Yield
With molybdenum peroxide hexamethylphosphorylamide In dichloromethane for 168h; Ambient temperature;	A 7% B 18% C 12%

methanol (67-56-1) + benzofuran-2(3H)-one (553-86-6) → methyl (2-hydroxyphenyl)acetate (22446-37-3)

Conditions	Yield
hydrogenchloride at 50℃; for 0.5h;	99%
With amberlyst-15 for 26h;	88%

benzofuran-2(3H)-one (553-86-6) → N-hydroxy-2-(2-hydroxyphenyl)acetamide (18639-02-6)

Conditions	Yield
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 0 - 20℃; Inert atmosphere;	99%

benzofuran-2(3H)-one (553-86-6) + (2S,5S)-2,5-bis(methoxymethyl)pyrrolidine (90290-05-4, 93621-94-4, 105016-60-2, 144993-81-7) → 1-[(2S,5S)-2,5-bis(methoxymethyl)pyrrolidin-1-yl]-2-(2-hydroxyphenyl)ethanone (1599446-48-6)

Conditions	Yield
In toluene Reflux;	99%

piperidine (110-89-4) + benzofuran-2(3H)-one (553-86-6) → 2-(2-hydroxyphenyl)-1-(piperidin-1-yl)ethan-1-one (24789-88-6)

Conditions	Yield
In toluene at 110℃;	98%
With toluene-4-sulfonic acid In toluene at 110℃;	98%

benzofuran-2(3H)-one (553-86-6) + salicylaldehyde (90-02-8) → 3-(2-hydroxyphenyl)-2H-chromen-2-one (13130-21-7)

Conditions	Yield
With triethylamine for 1h; Reflux;	98%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Reagent/catalyst; Sealed tube;	97%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%

benzofuran-2(3H)-one (553-86-6) + C16H14ClNO (1486473-80-6) → (3S*,11b'S*)-3'-chloro-6',7',11b',13'-tetrahydro-2H-spiro[benzofuran-3,12'-isoquinolino[2,1-a]quinolin]-2-one

Conditions	Yield
With piperidine In N,N-dimethyl acetamide at 150℃; for 4h; Inert atmosphere; diastereoselective reaction;	98%

benzofuran-2(3H)-one (553-86-6) + 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzaldehyde (124525-62-8) → (3S*,11b'S*)-9',10'-dimethoxy-6',7',11b',13'-tetrahydro-2H-spiro[benzofuran-3,12'-isoquinolino[2,1-a]quinolin]-2-one

Conditions	Yield
With piperidine In N,N-dimethyl acetamide at 150℃; for 5h; Inert atmosphere; diastereoselective reaction;	98%

benzofuran-2(3H)-one (553-86-6) + C15H13BrN2O → (3S*,11b'S*)-2'-bromo-6',7',11b',13'-tetrahydro-2H-spiro[benzofuran-3,12'-isoquinolino[2,1-a][1,8]naphthyridin]-2-one

Conditions	Yield
With piperidine In N,N-dimethyl acetamide at 150℃; for 7h; Inert atmosphere; diastereoselective reaction;	98%

benzofuran-2(3H)-one (553-86-6) + buta-2,3-dienoic acid benzyl ester (187661-86-5) → benzyl (E)-4-(3-(4-(benzyloxy)-4-oxobut-1-en-2-yl)-2-oxo-2,3-dihydrobenzofuran-3-yl)but-2-enoate

Conditions	Yield
With triphenylphosphine In toluene at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	97%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + benzofuran-2(3H)-one (553-86-6) → 3-(2-hydroxyphenyl)-6-methoxy-2H-chromen-2-one

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%
With triethylamine for 1h; Reflux;	96%

benzofuran-2(3H)-one (553-86-6) + 2-hydroxy-5-methylbenzaldehyde (613-84-3) → 3-(2-hydroxyphenyl)-6-methyl-2H-chromen-2-one (1338596-79-4)

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%
With triethylamine for 1h; Reflux;	90%

benzofuran-2(3H)-one (553-86-6) + 2-fluoro-6-hydroxybenzaldehyde (38226-10-7) → 5-fluoro-3-(2-hydroxyphenyl)coumarin

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	97%

benzofuran-2(3H)-one (553-86-6) + trimethyl orthoformate (149-73-5) → 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6)

Conditions	Yield
With acetic anhydride at 95 - 100℃; Concentration;	96.5%
With acetic anhydride at 40 - 90℃; Temperature;	96.8%
at 110℃; for 21h; Large scale;
With zinc(II) chloride at 110℃; for 4h;

benzofuran-2(3H)-one (553-86-6) → 2-(2-hydroxyphenyl)ethanol (7768-28-7)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;	96%
With lithium aluminium tetrahydride In diethyl ether Heating;
With sodium tetrahydroborate In tetrahydrofuran at 0 - 30℃; for 5h; Reagent/catalyst; Solvent; Temperature;	9.1 g

benzofuran-2(3H)-one (553-86-6) + diethylamine (109-89-7) → N,N-diethyl-2-(2-hydroxy)phenyl acetamide (182962-47-6)

Conditions	Yield
In toluene at 110℃;	96%
With toluene-4-sulfonic acid In toluene at 110℃;	96%

benzofuran-2(3H)-one (553-86-6) + ethylenediamine (107-15-3) → N,N'-(ethane-1,2-diyl)bis(2-(2-hydroxyphenyl)acetamide)

Conditions	Yield
In ethanol at 20℃; Inert atmosphere;	95%

benzofuran-2(3H)-one (553-86-6) + (S)-1-phenyl-ethylamine (2627-86-3) → 2-(2-hydroxyphenyl)-N-(1S-α-phenylethyl)acetamide (543681-05-6)

Conditions	Yield
In toluene at 20℃; for 0.0833333h;	95%
In toluene Heating;

benzofuran-2(3H)-one (553-86-6) + 1,5-bis(4-trifluoromethylphenyl)-1,4-pentadiene-3-one (103836-71-1, 103836-73-3, 103836-74-4, 42160-07-6) → C27H18F6O3

Conditions	Yield
With QD-4 In para-xylene at 20℃; for 96h; Catalytic behavior; Michael Addition; stereoselective reaction;	95%

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + benzofuran-2(3H)-one (553-86-6) → 3-(2-hydroxyphenyl)-7-methoxy-2H-chromen-2-one

Conditions	Yield
With triethylamine for 1h; Reflux;	95%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	95%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	95%

benzofuran-2(3H)-one (553-86-6) + 5-Nitrosalicylaldehyde (97-51-8) → 3-(2-hydroxyphenyl)-6-nitro-2H-chromen-2-one (13130-30-8)

Conditions	Yield
With triethylamine for 1h; Reflux;	95%

benzofuran-2(3H)-one (553-86-6) + 4-fluoro-2-hydroxybenzaldehyde (348-28-7) → 7-fluoro-3-(2-hydroxyphenyl)coumarin

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	95%
With N,N,N',N'-tetramethylguanidine In chloroform at 20℃; for 3h; Sealed tube;	95%

benzofuran-2(3H)-one (553-86-6) + carbon monoxide (201230-82-2) → 3-hydroxymethylenebenzofuran-2(3H)-one (70450-82-7)

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 40℃; under 225023 Torr; for 6h; Reagent/catalyst; Solvent; Temperature; Pressure; Green chemistry;	95%

benzofuran-2(3H)-one (553-86-6) + (Dimethylamino)ethoxyacetaldehyd-dimethylhydrazon (99412-47-2) → 3-<2-(Dimethylhydrazono)ethyliden>-2(3H)-benzofuranon

Conditions	Yield
In ethanol Ambient temperature;	94%

Upstream product

• 21119-50-6 2-diazo-1-phenylethan-1-one 
• 496-16-2 2.3-dihydrobenzofuran 
• 201230-82-2 carbon monoxide 
• 90-01-7 salicylic alcohol 
• 271-89-6 1-benzofurane 
• 85630-35-9 N,N-diethyl-2-methylcarbamoyloxybenzene 
• 133642-10-1 C₁₂H₁₉N₂O₄P 
• 103-82-2 phenylacetic acid 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 4525-75-1 2-chlorophenyl acetate 
• 105-53-3 diethyl malonate 
• 108-24-7 acetic anhydride 
• 496-64-0 3-hydroxy-2-pyrone 
• 34805-49-7 methyl 3-nitrobut-3-enoate 

Downstream Products

• 102273-29-0 (2-(hydroxymethyl)phenyl)(piperidin-1-yl)methanone 
• 93612-81-8 tetra-n-butylammonium 2-(hydroxymethyl)benzoate 
• 139061-42-0 (E)-2-(2-Hydroxy-phenyl)-3-pyridin-2-yl-acrylic acid methyl ester 
• 139061-43-1 (E)-3-Furan-2-yl-2-(2-hydroxy-phenyl)-acrylic acid methyl ester 
• 1839-72-1 2-phenylbenzofuran 
• 40800-85-9 3-benzoyl-3H-benzofuran-2-one 
• 27356-33-8 2-(2-methoxyphenyl)-1-phenylethan-1-one 
• 100880-56-6 2-oxo-2,3-dihydro-benzofuran-3-carbaldehyde-phenylhydrazone 
• 40800-90-6 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone 
• 1260119-54-7 3-(diphenylsulfuranylidene)benzofuran-2(3H)-one 
• 1297848-10-2 3-(bis(4-(dimethylamino)phenyl)methyl)benzofuran-2(3H)-one 

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Pd(II)-catalyzed ortho -C-H oxidation of arylacetic acid derivatives: Synthesis of benzofuranones

Pd(II)-catalyzed ortho-C-H acetoxylation of arylacetic acid derivatives is demonstrated with the aid of a novel S-methyl-S-2-pyridylsulfoximine (MPyS) directing group (DG). The α-mono- and α-unsubstituted arylacetic acid derivatives were readily employed in the ortho-C-H acetoxylations. The oxidation products are hydrolyzed, and the MPyS-DG is easily recovered, providing ready access to o-hydroxyarylacetic acids. 3-Mono- and 3-unsubstituted benzofuranones are synthesized from o-hydroxyarylacetic acids.

Regioselective Synthesis of Benzofuranones and Benzofurans

Reaction of 3-hydroxy-2-pyrones with nitroalkenes bearing ester groups gives benzofuranones. The reaction allows regioselective preparation of the benzofuranones with programmable substitution at any position. Complex substitution patterns are readily cre

Synthetic method of benzofuranone

The invention provides a synthetic method of benzofuranone. According to the method, o-cresol which is relatively easy to obtain is used as an initial raw material, and the target product benzofuranone is prepared through four-step reaction; and the whole preparation process is mild in condition, high in yield, easy to operate, small in environmental pollution and suitable for large-scale industrial production.