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

Description

3-Isochromanone is an organic compound that has been isolated from the fungus Nigrospora sp. PSU-F12. It is known for its chemical properties, which include forming lamellae. An improved Knoevenagel condensation of 3-isochromanone with aromatic aldehydes has been achieved through microwave irradiation on solid supports in the presence of various catalysts. Additionally, the synthesis of 3-isochromanone via Beayer-Villiger rearrangement has been reported.

Uses

Used in Pharmaceutical Industry:
3-Isochromanone is used as a starting reagent for the synthesis of BDPBI (7-bromo-1,4-dihydro-2-phenyl-4,4-bis(4-pyridinylmethyl)2H-isoquinolin-3-one dihydrochloride), which is a compound of interest in the pharmaceutical industry due to its potential applications in drug development and therapeutics.
Used in Chemical Synthesis:
3-Isochromanone serves as a valuable intermediate in the synthesis of various organic compounds. Its improved Knoevenagel condensation with aromatic aldehydes, achieved through microwave irradiation on solid supports and the presence of catalysts, highlights its utility in chemical synthesis processes.
Used in Research and Development:
The synthesis of 3-isochromanone via Beayer-Villiger rearrangement has been reported, making it a subject of interest for researchers and scientists working on new methods and techniques in organic chemistry. 3-ISOCHROMANONE's unique properties and synthesis pathways contribute to the advancement of knowledge in the field.

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

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

• 172-57-6 3H-3,8A-methano-benzo[c][1,2]dioxin 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 408535-88-6 (2-methoxymethyl-phenyl)-acetonitrile 
• 857570-88-8 (2-methoxymethyl-phenyl)-acetyl chloride 
• 95-13-6 1-indene 
• 615-13-4 2-indanone 
• 74897-57-7 trispiro<1,2,4,5,7,8-hexoxonan-3,2':6,2'':9,2'''-tris-indan> 
• 941-69-5 N-phenyl-maleimide 
• 163222-89-7 1,2-dihydrocyclobutabenzene-1-carboxylic acid 
• 64256-63-9 3,3-dimethoxy-isochroman 
• 67519-22-6 α-hydroxy-α'-cyano-o-xylene 
• 201230-82-2 carbon monoxide 
• 74785-02-7 (2-(bromomethyl)phenyl)methanol 
• 52267-51-3 benzyl diazoacetate 

Downstream Products

• 64795-09-1 N-<2-(3-indolyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide 
• 156004-09-0 (2-methoxymethyl-phenyl)-acetic acid methyl ester 
• 98988-20-6 N-<2-(4-benzyloxy-3-methoxyphenyl)-ethyl>-(2-hydroxymethyl)phenylacetamide 
• 98988-21-7 N-<2-(3-benzyloxy-4-methoxyphenyl)-ethyl>-(2-hydroxymethyl)phenylacetamide 
• 110409-93-3 (E)-4-(phenylmethylene)-3-isochromanone 
• 110409-94-4 (Z)-4-(phenylmethylene)-3-isochromanone 
• 32255-42-8 N-<2-(3,4-dimethoxyphenyl)-ethyl>-2-(hydroxymethyl)-phenylacetamide 
• 694-87-1 benzocyclobutene 
• 13737-35-4 o-(bromomethyl)phenylacetic acid 
• 42900-89-0 3,4-dihydro-1H-2-benzopyran-3-ol 
• 166537-41-3 N-<3-(3,4-Dimethoxyphenyl)propyl><2-(hydroxymethyl)phenyl>acetamid 
• 6772-69-6 2-p-tolyl-1,4-dihydro-2H-isoquinolin-3-one 
• 6772-72-1 2-(4-methoxy-phenyl)-1,4-dihydro-2H-isoquinolin-3-one 
• 6772-68-5 2-phenyl-1,4-dihydroisoquinolin-3(2H)-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.

(Cyclopentadienone)iron-Catalyzed Transfer Dehydrogenation of Symmetrical and Unsymmetrical Diols to Lactones

Air-stable iron carbonyl compounds bearing cyclopentadienone ligands with varying substitution were explored as catalysts in dehydrogenative diol lactonization reactions using acetone as both the solvent and hydrogen acceptor. Two catalysts with trimethylsilyl groups in the 2- A nd 5-positions, [2,5-(SiMe3)2-3,4-(CH2)4(δ4-C4C= O)]Fe(CO)3 (1) and [2,5-(SiMe3)2-3,4-(CH2)3(δ4-C4C= O)]Fe(CO)3 (2), were found to be the most active, with 2 being the most selective in the lactonization of diols containing both primary and secondary alcohols. Lactones containing five-, six-, and seven-membered rings were successfully synthesized, and no over-oxidations to carboxylic acids were detected. The lactonization of unsymmetrical diols containing two primary alcohols occurred with catalyst 1, but selectivity was low based on alcohol electronics and modest based on alcohol sterics. Evidence for a transfer dehydrogenation mechanism was found, and insight into the origin of selectivity in the lactonization of 1°/2° diols was obtained. Additionally, spectroscopic evidence for a trimethylamine-ligated iron species formed in solution during the reaction was discovered.