4385-35-7

Basic information

• Product Name: 3-ISOCHROMANONE
• Synonyms: ISOCHROMAN-3-ONE;3-ISOCHROMANONE;1,4-DIHYDRO-3H-2-BENZOPYRAN-3-ONE;3-ISOCHROMANONE 99+%;3,4-Dihydro-1H-2-benzopyran-3-one;3-Isochromanone ,98.5%;3-lsochroManone;2-HydroxyMethylphenylaceticacid lactone
• CAS NO: 4385-35-7
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• EINECS: 224-493-9
• Product Categories: Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 4385-35-7.mol
• Article Data: 53

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 130 °C / 1mmHg
• Flash Point: 137.7 °C
• Appearance: /
• Density: 1.196 g/cm³
• Vapor Pressure: 0.000144mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly, Heated, Sonicated), Methanol (Slightly)
• Water Solubility: 易溶于丙酮,甲醇,二氯乙烷等有机溶剂
• BRN: 123692
• CAS DataBase Reference: 3-ISOCHROMANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ISOCHROMANONE(4385-35-7)
• EPA Substance Registry System: 3-ISOCHROMANONE(4385-35-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4385-35-7(Hazardous Substances Data)

Usage

Chemical Properties

Lamellae

Uses

3-Isochromanone may be used as starting reagent in the synthesis of of BDPBI (7-bromo-1,4-dihydro-2-phenyl-4,4-bis(4-pyridinylmethyl)2H-isoquinolin-3-one dihydrochloride).

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 4193, 1980 DOI: 10.1021/ja00532a034Tetrahedron Letters, 36, p. 8123, 1995 DOI: 10.1016/0040-4039(95)01692-B

General Description

3-Isochromanone has been reported to be isolated from the fungus Nigrospora sp. PSU-F12. An improved Knoevenagel condensation of 3-isochromanone with aromatic aldehydes has been achieved by microwave irradiation on solid supports in the presence of various catalysts. Synthesis of 3-isochromanone via Beayer-Villiger rearrangement has been reported.

InChI:InChI=1/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2

Synthetic route

carbon monoxide (201230-82-2) + (2-(bromomethyl)phenyl)methanol (74785-02-7) → isochroman-3-one (4385-35-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; C52H46O2P2Pd2; triphenylphosphine In toluene at 60℃; under 760.051 Torr; for 2.16667h; Conversion of starting material;	100%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 25℃; under 760 Torr; for 24h;	71%

α,α'-dibromo-o-xylene (91-13-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
In tert-butyl alcohol	95.1%
Multi-step reaction with 3 steps 1: methanol 2: zinc chloride; tetrachloromethane / Erhitzen des Reaktionsprodukts mit Kaliumcyanid in wss. Aethanol 3: aqueous sulfuric acid View Scheme

α-chloro-α'-cyano-o-xylene (98590-71-7) → isochroman-3-one (4385-35-7) + α-hydroxy-α'-cyano-o-xylene (67519-22-6)

Conditions	Yield
With hydrogenchloride In water at 150℃; under 3677.86 Torr; for 3h;	A 95% B n/a

2-indanone (615-13-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 240h;	90%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h; Ambient temperature;	90%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	90%

carbon monoxide (201230-82-2) + phthalyl alcohol (612-14-6) → isochroman-3-one (4385-35-7) + o-xylene (95-47-6) + o-methylphenylacetic acid (644-36-0)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 88% B n/a C 9%
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 13% B n/a C 52%

carbon monoxide (201230-82-2) + o-Xylylene dichloride (612-12-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
With water; N-ethyl-N,N-diisopropylamine In tert-Amyl alcohol at 40 - 70℃; under 3087.28 - 3475.15 Torr; Product distribution / selectivity;	84.53%
With water; N-ethyl-N,N-diisopropylamine In tert-Amyl alcohol at 70℃; under 1551.49 Torr; Product distribution / selectivity;	80.95%
With water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dichloride In tert-Amyl alcohol at 70 - 75℃; under 3863.02 Torr; for 4h; Product distribution / selectivity;	75.4%
With water; N-ethyl-N,N-diisopropylamine; hydrogen tetrachloropalladate; triphenylphosphine In tert-Amyl alcohol at 70℃; under 3102.97 - 3863.02 Torr; for 2 - 4h; Product distribution / selectivity;	69.9%

2-chloromethylphenylacetic acid (95335-46-9) → isochroman-3-one (4385-35-7)

Conditions	Yield
With sodium hydrogencarbonate In water at 50℃; for 0.5h; Temperature;	84.1%
With hydrogenchloride; potassium hydrogencarbonate In fluorobenzene; cyclohexane
With potassium hydrogencarbonate In water at 50℃; pH=7.2; pH-value; Temperature; Reagent/catalyst;	39 g

tert-Amyl alcohol (75-85-4) + o-Xylylene dichloride (612-12-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dihydrotetrachloropalladium (H2PdCl4) In o-xylene; water	83.9%

1,3-dihydroisobenzofuran (496-14-0) + carbon dioxide (124-38-9) → isochroman-3-one (4385-35-7)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran 1.) 20 deg C, 0.5 h; 2.) -78 deg C, 1 h;	82%
With naphthalene; lithium 1.) THF, 0 deg C, 2 h, 2.) THF, -40 deg C, 5 min; Yield given. Multistep reaction;
With naphthalene; lithium 1) THF, 0 deg C, 1.5 h, 2) THF, -40 deg C, 5 min; Yield given. Multistep reaction;

α-chloro-α'-cyano-o-xylene (98590-71-7) → isochroman-3-one (4385-35-7) + α-carboxy-α'-hydroxy-o-xylene + α-aminocarboxy-α'-hydroxy-o-xylene + α-hydroxy-α'-cyano-o-xylene (67519-22-6)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 6h;	A 76% B n/a C n/a D n/a
In water at 150℃; under 3677.86 Torr; for 3h;	A 75% B n/a C n/a D n/a

tert-Amyl alcohol (75-85-4) + o-Xylylene dichloride (612-12-4) + N-ethyl-N,N-diisopropylamine (7087-68-5) → isochroman-3-one (4385-35-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; triphenylphosphine; dihydrotetrachloropalladium (H2PdCl4) In o-xylene; water	75.8%

tert-Amyl alcohol (75-85-4) + o-Xylylene dichloride (612-12-4) + triphenylphosphine (603-35-0) → isochroman-3-one (4385-35-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; carbon monoxide; N-ethyl-N,N-diisopropylamine; palladium(II) chloride In water	75.4%

2-(ethoxycarbonylmethyl)benzoic acid (22479-46-5) → isochroman-3-one (4385-35-7)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 40℃; Inert atmosphere;	75%

o-Xylylene dichloride (612-12-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
With hydrogenchloride; calcium hydroxide; carbon monoxide; triphenylphosphine In water; dichlorobis(triphenylphosphine)palladium[II]; tert-butyl alcohol	72.9%
palladium(II) chloride In 1-methyl-pyrrolidin-2-one; water; tert-butyl alcohol	66.4%
With hydrogenchloride; sodium hydroxide; carbon monoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium chloride (PdCl2) In o-xylene; water; tert-butyl alcohol

(±)-methyl 2-((3aR,6R,7aR)-1-oxo-6,7-dihydro-3H-3a,6-epoxyisobenzofuran-7a(1H)-yl)acetate → isochroman-3-one (4385-35-7)

Conditions	Yield
With trifluorormethanesulfonic acid In chloroform at 80℃; for 2h;	70%

N-phenyl-maleimide (941-69-5) + 1,2-dihydrocyclobutabenzene-1-carboxylic acid (163222-89-7, 163222-90-0) → isochroman-3-one (4385-35-7) + (3aR,4S,9aR)-1,3-Dioxo-2-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid (138235-90-2, 138331-82-5) + (3aS,4S,9aS)-1,3-Dioxo-2-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid (138235-90-2, 138331-82-5)

Conditions	Yield
In benzene-d6 at 140℃; for 3h;	A 19% B 13% C 68%

o-methylphenylacetic acid (644-36-0) → isochroman-3-one (4385-35-7)

Conditions	Yield
Stage #1: o-methylphenylacetic acid With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) In fluorobenzene at 75 - 80℃; for 4h; Stage #2: With potassium hydroxide; potassium hydrogencarbonate; potassium iodide In fluorobenzene; water at 60℃; pH=6.3; Conversion of starting material;	68%
With iodobenzene; 3-chloro-benzenecarboperoxoic acid; potassium bromide In 2,2,2-trifluoroethanol at 20℃; for 24h;	67%
Stage #1: o-methylphenylacetic acid With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 75 - 80℃; for 4h; Stage #2: With potassium hydroxide; potassium hydrogencarbonate; potassium iodide In water; chlorobenzene at 60℃; pH=6.5; Conversion of starting material;	61.5%

o-(methoxycarbonylmethyl)benzoic acid (14736-50-6) → isochroman-3-one (4385-35-7)

Conditions	Yield
Stage #1: o-(methoxycarbonylmethyl)benzoic acid With borane In tetrahydrofuran at -15 - 20℃; for 16h; Stage #2: With toluene-4-sulfonic acid In toluene at 80℃; for 3h;	66%

(±)-2-((3aR,6R,7aR)-1-oxo-6,7-dihydro-3H-3a,6-epoxyisobenzofuran-7a(1H)-yl)acetic acid → isochroman-3-one (4385-35-7)

Conditions	Yield
With trifluorormethanesulfonic acid In chloroform	65%

2-(2-hydroxyethyl)benzyl alcohol (6346-00-5) → isochroman-3-one (4385-35-7) + isochroman-1-one (4702-34-5)

Conditions	Yield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h; regioselective reaction;	A 18% B 58%
With iodosylbenzene; potassium bromide In water for 2h; sonication;
With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2 In water for 20h; Inert atmosphere; Reflux; Green chemistry; Overall yield = 88 %;

benzyl diazoacetate (52267-51-3) → isochroman-3-one (4385-35-7)

Conditions	Yield
dirhodium tetraacetate In dichloromethane for 24h;	56%

carbon monoxide (201230-82-2) + phthalyl alcohol (612-14-6) → isochroman-3-one (4385-35-7) + o-methylphenylacetic acid (644-36-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;	A 56% B 9 % Spectr.

2-methyl-benzyl alcohol (89-95-2) + CO2 → isochroman-3-one (4385-35-7)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane 1) 24 h, room temp. or 4 h reflux;	53%

formic acid (64-18-6) + o-Xylylene dichloride (612-12-4) → isochroman-3-one (4385-35-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 12h; Inert atmosphere;	46%

o-Xylylene dichloride (612-12-4) + triphenylphosphine (603-35-0) → isochroman-3-one (4385-35-7)

Conditions	Yield
palladium(II) chloride In water; tert-butyl alcohol	24%

α-chloro-α'-cyano-o-xylene (98590-71-7) → isochroman-3-one (4385-35-7)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 6h;	3%

3H-3,8A-methano-benzo[c][1,2]dioxin (172-57-6) + 1-methyl-4-nitrosobenzene (623-11-0) → isochroman-3-one (4385-35-7)

(2-methoxymethyl-phenyl)-acetonitrile (408535-88-6) → isochroman-3-one (4385-35-7)

Conditions	Yield
With hydrogen bromide
With sulfuric acid

methanol (67-56-1) + isochroman-3-one (4385-35-7) → methyl 2-(chloromethyl)phenylacetate (95360-33-1)

Conditions	Yield
With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 30℃; for 4h; Solvent;	100%
With hydrogenchloride at 20 - 26℃; for 2.5h;	98%
With thionyl chloride at 20℃; Cooling with ice;	96%

chloro-trimethyl-silane (75-77-4) + isochroman-3-one (4385-35-7) → ((1H-isochromen-3-yl)oxy)trimethylsilane (87532-04-5)

Conditions	Yield
Stage #1: isochroman-3-one With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Enzymatic reaction;	99%
With n-butyllithium; diisopropylamine 1.) THF, -78 deg C, 10 min, 2.) 3 h, warm. to RT; Yield given. Multistep reaction;

isochroman-3-one (4385-35-7) + methylamine (74-89-5) → 2-(2-(hydroxymethyl)phenyl)-N-methylacetamide (218131-53-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 8h;	99%
In tetrahydrofuran at 20℃; for 8h;	93%

isochroman-3-one (4385-35-7) → 2-(2-hydroxyethyl)benzyl alcohol (6346-00-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	99%
With phenylsilane; potassium hydroxide In tetrahydrofuran for 4h; Schlenk technique; Inert atmosphere; Reflux;	60%
With samarium diiodide; water In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	65 %Spectr.

isochroman-3-one (4385-35-7) + ethanol (64-17-5) → ethyl 2-(2-(bromomethyl)phenyl)acetate (39191-76-9)

Conditions	Yield
With phosphorus tribromide	98%
With hydrogen bromide	90%
With hydrogen bromide at 20℃; for 48h; Ring cleavage; esterification;

isochroman-3-one (4385-35-7) → methyl 2-(chloromethyl)phenylacetate (95360-33-1)

Conditions	Yield
With hydrogenchloride In methanol; dichloromethane	98%
With thionyl chloride; potassium hydrogencarbonate In methanol; toluene
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Reflux; Heating 2: 1 h / 20 °C / Cooling with ice View Scheme

isochroman-3-one (4385-35-7) → o-methylphenylacetic acid (644-36-0)

Conditions	Yield
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 50℃; under 760.051 Torr; for 12h;	98%
With palladium on activated carbon; W(OTf)6; hydrogen In acetic acid at 50℃; under 760.051 Torr; for 12h;	97%

isochroman-3-one (4385-35-7) + 2-methyl-benzyl alcohol (89-95-2) → 3-[(2'-hydroxymethyl)phenyl]coumarin

Conditions	Yield
With piperidine at 140℃; for 1h; Knoevenagel condensation;	97%

isochroman-3-one (4385-35-7) + 4-chlorobenzylamine (104-86-9) → 1,4-dihydro-2-(4-chlorophenylmethyl)-3(2H)-isoquinolinone

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;	97%

isochroman-3-one (4385-35-7) → 4-diazo-3-isochromanone

Conditions	Yield
Stage #1: isochroman-3-one With sodium azide; p-toluenesulfonyl chloride In acetonitrile at 20℃; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃;	96%
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃;	81%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 1h;	60%

isochroman-3-one (4385-35-7) + Methyl formate (107-31-3) → methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate (117428-51-0)

Conditions	Yield
With acetic acid Heating;	96%

isochroman-3-one (4385-35-7) + para-methylbenzylamine (104-84-7) → 1,4-dihydro-2-(4-methylphenylmethyl)-3(2H)-isoquinolinone

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;	95%

isochroman-3-one (4385-35-7) → 3,4-dihydro-1H-2-benzopyran-3-ol (42900-89-0)

Conditions	Yield
With diisobutylaluminium hydride In toluene at -60 - -10℃;	94%
With diisobutylaluminium hydride In dichloromethane at -78℃; for 3h;	91%
With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1h; Reduction;
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 2h;
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; Inert atmosphere;

isochroman-3-one (4385-35-7) → o-(bromomethyl)phenylacetic acid (13737-35-4)

Conditions	Yield
With hydrogen bromide In acetic acid	93%
With hydrogen bromide In acetic acid at 20 - 70℃; for 3h;	93%
With hydrogen bromide; acetic acid at 70℃; for 1h;	88%
With hydrogen bromide In acetic acid 1.) 20 deg C, 2 h; 2.) 70 deg C, 1 h;
With hydrogen bromide In water

isochroman-3-one (4385-35-7) + 3-(3,4-dimethoxyphenyl)propylamine (14773-42-3) → N-<3-(3,4-Dimethoxyphenyl)propyl><2-(hydroxymethyl)phenyl>acetamid (166537-41-3)

Conditions	Yield
In ethanol for 3h; Heating;	92%

isochroman-3-one (4385-35-7) + benzylamine (100-46-9) → 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone (6772-73-2)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;	92%
With aluminium trichloride at 160℃; for 20h;	73%

isochroman-3-one (4385-35-7) + methyl iodide (74-88-4) → 3,4-dihydro-4-methyl-(3H)-2-benzopyran-3-one (122571-80-6)

Conditions	Yield
Stage #1: isochroman-3-one With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: methyl iodide at -78℃; for 1h;	90%

isochroman-3-one (4385-35-7) + trimethyl orthoformate (149-73-5) → (E)-3,3-dimethoxy-4-(methoxymethylene)isochroman

Conditions	Yield
With boron trifluoride diethyl etherate In methanol at 40℃; for 24h; Solvent; Temperature; Concentration; Reagent/catalyst;	90%

isochroman-3-one (4385-35-7) + 3-(3-methoxyphenyl)propan-1-amine (18655-52-2) → <2-(Hydroxymethyl)phenyl>-N-<3-(3-methoxyphenyl)propyl>acetamid

Conditions	Yield
In ethanol for 3h; Heating;	88%

isochroman-3-one (4385-35-7) + 2-methoxyacetonitrile (1738-36-9) → C12H13NO3 (1179322-20-3)

Conditions	Yield
With heptahydridobis(triphenylphosphine)rhenium In tetrahydrofuran at 150℃; for 5h; Inert atmosphere; teflon-cocked sealed tube;	88%

isochroman-3-one (4385-35-7) + cyclohexa-1,3-diene (1165952-91-9) → 4-(cyclohex-2-enyl)isochroman-3-one

Conditions	Yield
With allyl(cyclopentadiene)palladium(II); 1,3-bis(dicyclohexylphosphine)propane In 1,2-dimethoxyethane at 80℃; for 18h;	87%

isochroman-3-one (4385-35-7) + ethyl cyanoformate (623-49-4) → ethyl 3-oxoisochroman-4-carboxylate (72206-74-7)

Conditions	Yield
Stage #1: isochroman-3-one With lithium diisopropyl amide Inert atmosphere; Stage #2: ethyl cyanoformate Claisen condensation;	87%

isochroman-3-one (4385-35-7) + 3-benzyloxy-4-methoxyphenylethylamine (36455-21-7) → N-<2-(3-benzyloxy-4-methoxyphenyl)-ethyl>-(2-hydroxymethyl)phenylacetamide (98988-21-7)

Conditions	Yield
In ethanol for 24h; Ambient temperature;	86%

isochroman-3-one (4385-35-7) + 4-methoxy-benzylamine (2393-23-9) → 1,4-dihydro-2-(4-methoxyphenylmethyl)-3(2H)-isoquinolinone

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;	85%

Upstream product

• 615-13-4 2-indanone 
• 408535-88-6 (2-methoxymethyl-phenyl)-acetonitrile 
• 172-57-6 3H-3,8A-methano-benzo[c][1,2]dioxin 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 22479-46-5 2-(ethoxycarbonylmethyl)benzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 22364-68-7 2-tolylmethylnitrile 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 95-47-6 o-xylene 
• 4370-02-9 cis-indane-1,2-diol 
• 95-13-6 1-indene 
• 64-18-6 formic acid 
• 612-12-4 o-Xylylene dichloride 
• 89-51-0 Homophthalic acid 

Downstream Products

• 39191-76-9 ethyl 2-(2-(bromomethyl)phenyl)acetate 
• 156004-09-0 (2-methoxymethyl-phenyl)-acetic acid methyl ester 
• 64795-09-1 N-<2-(3-indolyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide 
• 13737-37-6 methyl 2-[2-(bromomethyl)phenyl]acetate 
• 6772-67-4 2-chloromethylphenylacetyl chloride 
• 428501-02-4 ethyl 2-(2-(azidomethyl)phenyl)acetate 
• 40360-71-2 anhydrolycorine-7-one 

Relevant articles and documents

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Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Regioselective biocatalytic self-sufficient Tishchenko-type reactionviaformal intramolecular hydride transfer

A self-sufficient nicotinamide-dependent intramolecular bio-Tishchenko-type reaction was developed. The reaction is catalyzed by alcohol dehydrogenases and proceeds through formal intramolecular hydride transfer on dialdehydes to deliver lactones. Regioselectivity on [1,1′-biphenyl]-2,2′-dicarbaldehyde substrates could be controlledviathe electronic properties of the substituents. Preparative scale synthesis provided access to substituted dibenzo[c,e]oxepin-5(7H)-ones.