4460-86-0

Basic information

• Product Name: 2,4,5-Trimethoxybenzaldehyde
• Synonyms: ASARONALDEHYDE;ASARALDEHYDE;2,4,5-TRIMETHOXYBENZALDEHYDE;3,4,6-trimethoxybenzaldehyde;AKOS BBS-00003175;2,4,5-trimethoxybenzaldehdye;2,4,5-Trimethoxy-benzaldehyd;2,4,5-Trimethoxybenzaldheyde
• CAS NO: 4460-86-0
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• EINECS: 224-713-3
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Aldehydes & Derivatives (substituted);Inhibitors
• Mol File: 4460-86-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 112-114 °C(lit.)
• Boiling Point: 140°C 4mm
• Flash Point: 140°C/4mm subl.
• Appearance: White to light beige/Fine Crystalline Powder
• Density: 1.2166 (rough estimate)
• Vapor Pressure: 0.000125mmHg at 25°C
• Refractive Index: 1.5550 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: <0.1 g/100 mL at 22℃
• Sensitive: Air Sensitive
• BRN: 1951403
• CAS DataBase Reference: 2,4,5-Trimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trimethoxybenzaldehyde(4460-86-0)
• EPA Substance Registry System: 2,4,5-Trimethoxybenzaldehyde(4460-86-0)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34
• Safety Statements: 22-24/25-45-36/37/39-27-26
• WGK Germany: 3
• RTECS: CU8460000
• TSCA: Yes
• Hazardous Substances Data: 4460-86-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light beige fine crystalline powder

Uses

Different sources of media describe the Uses of 4460-86-0 differently. You can refer to the following data:
1. fly attractant
2. 2,4,5-Trimethoxybenzaldehyde is used in the synthesis of stilbene and hydrostibene derivatives as potential anticancer agents, inhibiting tubulin. Also used in the synthesis of HIV-RT inhibitors.
3. A selective Cox-2 inhibitor.

General Description

Beige powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,4,5-Trimethoxybenzaldehyde is light sensitive. .

Health Hazard

SYMPTOMS: Symptoms of exposure to related compounds are skin and gastrointestinal tract irritation, sensitization, blistering, nausea, vomiting, diarrhea, urinary tract irritation, initial excitement, convulsions and central nervous system depression.

Fire Hazard

Flash point data for 2,4,5-Trimethoxybenzaldehyde are not available, but 2,4,5-Trimethoxybenzaldehyde is probably combustible.

InChI:InChI=1/C10H12O4/c1-12-8-5-10(14-3)9(13-2)4-7(8)6-11/h4-6H,1-3H3

Synthetic route

difluoromethyl phenyl sulfide (1535-67-7) + 1,2,4-trimethoxy-benzene (135-77-3) → asaraldehyde (4460-86-0)

Conditions	Yield
Stage #1: difluoromethyl phenyl sulfide; 1,2,4-trimethoxy-benzene With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane; water; dimethyl sulfoxide at 20℃; for 2h;	98%

(2,4,5-trimethoxyphenyl)methanol (30038-31-4) → asaraldehyde (4460-86-0)

Conditions	Yield
With copper(l) iodide; TEMPOL; N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	97%
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane at 0℃; for 1.5h; Molecular sieve; Inert atmosphere;	96%
With tert.-butylhydroperoxide; eosin y In decane; acetonitrile at 25℃; for 36h; Inert atmosphere; Irradiation; Molecular sieve; Green chemistry; chemoselective reaction;	87%

α-asarone (2883-98-9) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water microwave irradiation;	84%
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water Microwave irradiation;	82%

asarone (494-40-6, 2883-98-9, 5273-86-9) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water at 100℃; Microwave irradiation;	83%
With chromium(VI) oxide
With potassium permanganate

C12H16O3 (5273-86-9) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water at 100℃; Microwave irradiation;	83%
With sodium periodate; osmium(VIII) oxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran; water for 0.0138889h; microwave irradiation;	82%
With dipyridinium dichromate; acetic acid In 1,4-dioxane for 0.333333h; Heating; Microwave irradiation;
With potassium permanganate; sodium hydrogencarbonate at 20℃;

1,2,4-trimethoxy-benzene (135-77-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → asaraldehyde (4460-86-0)

Conditions	Yield
With trichlorophosphate at 20℃; for 1h; Vilsmeier reaction;	81%
With trichlorophosphate at 0 - 80℃; for 3h; Vilsmeier-Haack Formylation; Inert atmosphere;	80%
With trichlorophosphate

acetic acid acetoxy-(2,4,5-trimethoxy-phenyl)-methyl ester → asaraldehyde (4460-86-0)

Conditions	Yield
With ammonium acetate for 0.0125h; microwave irradiation;	77%

C16H18N2O3 (324067-40-5) → asaraldehyde (4460-86-0) + 4,5-bis(2,4,5-trimethoxyphenyl)-2-phenyl-2H-1,2,3-triazole (1376268-31-3)

Conditions	Yield
With copper(II) acetate monohydrate In toluene at 60℃; for 7h;	A n/a B 66%

N-(chloromethyl)diformamide (877680-53-0) + 1,2,4-trimethoxy-benzene (135-77-3) → asaraldehyde (4460-86-0) + tris(2,4,5-trimethoxyphenyl)methane (14470-07-6)

Conditions	Yield
With aluminum (III) chloride In chlorobenzene at 0 - 18℃; for 22h;	A 56% B 24%

5-ethenyl-1,2,4-trimethoxybenzene (17598-03-7) → asaraldehyde (4460-86-0)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation;	52%

1,2,4-trimethoxy-benzene (135-77-3) + trimethyl orthoformate (149-73-5) → asaraldehyde (4460-86-0) + tris(2,4,5-trimethoxyphenyl)methane (14470-07-6)

Conditions	Yield
With boron trifluoride diethyl etherate In neat liquid at 20℃; for 1h; Friedel-Crafts Alkylation;	A 30% B 46%

difluoromethyl phenyl sulfide (1535-67-7) + 1,2,4-trimethoxy-benzene (135-77-3) → asaraldehyde (4460-86-0) + bis(2,4,5-trimethoxyphenyl)phenylsulfanylmethane + 1-(diphenylsulfanylmethyl)-2,4,5-trimethoxybenzene

Conditions	Yield
With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	A 37% B 6% C 42%
With aluminum (III) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	A 7% B 23% C 6%

methanol (67-56-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → asaraldehyde (4460-86-0)

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate; 3-trifluoromethylaniline In dichloromethane at 60℃; for 24h; Sealed tube;	33%

difluoromethyl phenyl sulfide (1535-67-7) + 1,2,4-trimethoxy-benzene (135-77-3) → asaraldehyde (4460-86-0) + tris(2,4,5-trimethoxyphenyl)methane (14470-07-6) + bis(2,4,5-trimethoxyphenyl)phenylsulfanylmethane + 1-(diphenylsulfanylmethyl)-2,4,5-trimethoxybenzene

Conditions	Yield
With titanium tetrachloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	A 20% B 3% C 24% D 25%

hydrogen cyanide (74-90-8) + 1,2,4-trimethoxy-benzene (135-77-3) → asaraldehyde (4460-86-0)

Conditions	Yield
With hydrogenchloride; aluminium trichloride; benzene at 40 - 50℃; Zersetzung des Reaktionsgemisches mit Eiswasser;

asarone (494-40-6, 2883-98-9, 5273-86-9) → asaraldehyde (4460-86-0) + asaronic acid (490-64-2)

Conditions	Yield
With potassium permanganate; water

2,4,5-trimethoxycinnamic acid (24160-53-0) → asaraldehyde (4460-86-0) + asaronic acid (490-64-2)

2,4-Dihydroxybenzaldehyde (95-01-2) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium hydroxide; dipotassium peroxodisulfate
Multi-step reaction with 3 steps 1: Br2; NaClO3 2: CuCl 3: NaOH View Scheme

2,4-dihydroxy-5-methoxybenzaldehyde (51061-83-7) + methyl iodide (74-88-4) → asaraldehyde (4460-86-0)

Conditions	Yield
With potassium carbonate; acetone

2-hydroxy-4,5-dimethoxybenzaldehyde (14382-91-3) + methyl iodide (74-88-4) → asaraldehyde (4460-86-0)

Conditions	Yield
With potassium carbonate; acetone

2,5-dihydroxy-4-methoxy-benzaldehyde (29865-97-2) + methyl iodide (74-88-4) → asaraldehyde (4460-86-0)

Conditions	Yield
With potassium carbonate; acetone

methanol (67-56-1) + α-asarone (2883-98-9) → C12H16O3 (5273-86-9) + asaraldehyde (4460-86-0) + 3-Methoxy-3-(2,4,5-trimethoxyphenyl)-propan (82645-86-1)

Conditions	Yield
for 4h; Irradiation;

C12H16O3 (5273-86-9) → α-asarone (2883-98-9) + asaraldehyde (4460-86-0) + andamanicin (73036-51-8) + (Z)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde (99217-07-9)

Conditions	Yield
for 720h; Irradiation; Further byproducts given;	A 0.26 g B 1.18 g C 0.28 g D 46 mg

C12H16O3 (5273-86-9) → α-asarone (2883-98-9) + asaraldehyde (4460-86-0) + andamanicin (73036-51-8) + (Z)-3-(2,4,5-trimethoxyphenyl)acrylaldehyde (99217-07-9) + trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8)

Conditions	Yield
for 720h; Mechanism; Irradiation;	A 0.26 g B 1.18 g C 0.28 g D 46 mg E 0.19 g

C12H16O3 (5273-86-9) → α-asarone (2883-98-9) + asaraldehyde (4460-86-0) + andamanicin (73036-51-8) + trans 2,4,5-trimethoxy cinnamaldehyde (99217-07-9, 106128-88-5, 99217-06-8)

Conditions	Yield
for 720h; Irradiation; Further byproducts given;	A 0.26 g B 1.18 g C 0.28 g D 0.19 g

1-allyl-2,4,5-trimethoxybenzene (5353-15-1) → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium dichromate In acetic acid; benzene for 6h; Heating;

calmus oil → asaraldehyde (4460-86-0)

Conditions	Yield
With sodium hydrogensulfite beim Stehen an der Luft;
With water; sodium hydrogensulfite

asarone (494-40-6, 2883-98-9, 5273-86-9) + acetic acid (64-19-7) + K2cr2O7 → asaraldehyde (4460-86-0)

asarone (494-40-6, 2883-98-9, 5273-86-9) + KMnO4 → asaraldehyde (4460-86-0) + asaronic acid (490-64-2)

2-acetyl-6-allylphenol (58621-39-9) + asaraldehyde (4460-86-0) → 1-(2-hydroxy-3-allyl-phenyl)-3-(2,4,5-trimethoxy-phenyl)-propenone

Conditions	Yield
With potassium hydroxide In ethanol for 191h;	100%
With potassium hydroxide In ethanol for 191h; aldol condensation;

asaraldehyde (4460-86-0) → 1,2,4-trimethoxy-5-methylbenzene (14894-74-7)

Conditions	Yield
With triethylsilane; chloro-trimethyl-silane In acetonitrile	100%
Multi-step reaction with 2 steps 1: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / 0.12 h / Irradiation 2: KOH / bis-(2-hydroxy-ethyl) ether / 0.28 h / Irradiation View Scheme

asaraldehyde (4460-86-0) + methylamine (74-89-5) → C11H15NO3 (1246401-41-1)

Conditions	Yield
at 20℃; for 12h;	100%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + asaraldehyde (4460-86-0) → 2,4,5-trimethoxycinnamic acid ethyl ester (14469-89-7)

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 20h; Horner-Wadsworth-Emmons reaction; Reflux;	100%

Nitroethane (79-24-3) + asaraldehyde (4460-86-0) → 2,4,5-trimethoxy-β-methyl-β-nitrostyrene (134040-35-0, 17231-84-4)

Conditions	Yield
With ammonium acetate for 0.75h; Reflux;	99.5%
With ammonium acetate
With ammonium acetate In acetic acid

asaraldehyde (4460-86-0) → 2-hydroxy-4,5-dimethoxybenzaldehyde (14382-91-3)

Conditions	Yield
Stage #1: asaraldehyde With boron trichloride In dichloromethane at -78 - 20℃; for 3h; Stage #2: With hydrogenchloride; water In dichloromethane at 0℃;	99%
With boron tribromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	99%
With boron trichloride In dichloromethane at -78 - 20℃; for 3h;	98%

asaraldehyde (4460-86-0) + 2-iodophenylamine (615-43-0) → N-(2,4,5-trimethoxybenzyl)-2-iodobenzenamine

Conditions	Yield
Stage #1: asaraldehyde; 2-iodophenylamine With acetic acid In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃; for 95h; Inert atmosphere;	99%

asaraldehyde (4460-86-0) + thiophenol (108-98-5) → 1-(diphenylsulfanylmethyl)-2,4,5-trimethoxybenzene

Conditions	Yield
With indium(III) bromide In water at 20℃; for 3h;	98%

N,N'-diacetylpiperazin-2,5-dione (3027-05-2) + asaraldehyde (4460-86-0) → 1-Acetyl-3-[1-(2,4,5-trimethoxy-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione (709615-05-4)

Conditions	Yield
With potassium tert-butylate; tert-butyl alcohol In dichloromethane at 20℃; for 4h;	98%

asaraldehyde (4460-86-0) + 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (139756-02-8) → 1-methyl-3-propyl-5-(2,4,5-trimethoxyphenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-(6H)-one (1610875-93-8)

Conditions	Yield
With dipotassium peroxodisulfate In water; dimethyl sulfoxide at 100℃; for 0.05h; Sealed tube; Microwave irradiation;	98%
Stage #1: asaraldehyde; 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide In ethanol at 60℃; for 0.5h; Stage #2: With oxygen; copper dichloride In ethanol at 75℃; for 0.5h;	87%

asaraldehyde (4460-86-0) → (2,4,5-trimethoxyphenyl)methanol (30038-31-4)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;	97%
With sodium tetrahydroborate In methanol for 0.5h;	84%
With ethanol; platinum Hydrogenation;

2,4-dimethylpent-3-ylamine (4083-57-2) + asaraldehyde (4460-86-0) → 2,4,5-Trimethoxybenzaldehyde 2,4-dimethylpent-3-ylimine

Conditions	Yield
	97%
With toluene-4-sulfonic acid In toluene for 3h; Heating / reflux;	96%
With toluene-4-sulfonic acid In toluene for 3h; Heating / reflux;	96%

(1-methoxyethyl)triphenylphosphonium tetrafluoroborate + asaraldehyde (4460-86-0) → 1-hydroxy-1-(2,4,5-trimethoxyphenyl)propan-2-one (1422453-77-7)

Conditions	Yield
Stage #1: (1-methoxyethyl)triphenylphosphonium tetrafluoroborate With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #2: asaraldehyde In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;	97%

phthalic anhydride (85-44-9) + asaraldehyde (4460-86-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl 3‑amino‑5,10‑dioxo‑1‑(2,4,5‑trimethoxyphenyl)‑5,10‑dihydro‑1H‑pyrazolo[1,2‑b]phthalazine‑2‑carboxylate

Conditions	Yield
With hydrazine hydrate In water at 60℃; for 0.666667h; Green chemistry;	97%

1-thiopropane (107-03-9) + asaraldehyde (4460-86-0) → 1-(bis-propylsulfanyl-methyl)-2,4,5-trimethoxy-benzene

Conditions	Yield
With indium(III) bromide In dichloromethane at 20℃; for 1h;	96%

asaraldehyde (4460-86-0) + Dimethyl succinate (106-65-0) → Asarylidenbernsteinsaeure (74018-30-7)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 2h; Heating;	96%

asaraldehyde (4460-86-0) + 4-bromo-4'-acetylbiphenyl (5731-01-1) → 1-[(4-(4-bromophenyl)phenyl)]-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (1256153-24-8)

Conditions	Yield
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation;	96%

asaraldehyde (4460-86-0) + 1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → (2E)-1-(2,4,6-trimethoxyphenyl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one (73694-37-8)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation;	96%
With lithium hydroxide monohydrate In ethanol at 20℃; for 168h; Claisen-Schmidt Condensation;	78%
With lithium hydroxide monohydrate In ethanol at 20℃; for 168h; Claisen-Schmidt Condensation;	78%
With potassium hydroxide at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Inert atmosphere;	68%

4,6-dimethoxycoumaranone (4225-35-8) + asaraldehyde (4460-86-0) → (Z)-benzylidene-4,6,2',4',5'-pentamethoxybenzylidenebenzofuran-3(2H)-one

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 0.5h;	95%
With potassium hydroxide In methanol at 20℃; for 1h;

3-(3',4',5'-trimethoxyphenyl)-4,5,6-trimethoxy-indan-1-one (1059117-37-1) + asaraldehyde (4460-86-0) → 3-(3',4',5'-trimethoxyphenyl)-4,5,6-trimethoxy-2-(2'',4'',5''-trimethoxybenzylidene)-indan-1-one (1375084-23-3)

Conditions	Yield
With potassium hydroxide In methanol at 20℃;	95%

asaraldehyde (4460-86-0) + acetophenone (98-86-2) → (2E)‑1‑phenyl‑3‑(2,4,5‑trimethoxyphenyl)prop‑2‑en‑1‑one (1393480-79-9)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation;	95%
With sodium hydroxide In ethanol at 20℃; for 3h; Claisen-Schmidt Condensation;	82%
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation;	79%
With sodium hydroxide In ethanol at 20℃; for 48h; Claisen-Schmidt Condensation;	74%
With sodium hydroxide at 20℃; for 48h; Claisen-Schmidt Condensation;	31%

asaraldehyde (4460-86-0) + 2,5-diacetoxyacetophenone (31405-72-8) → (E)-1-(2,5-Dicetoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation;	95%

phthalic anhydride (85-44-9) + asaraldehyde (4460-86-0) + malononitrile (109-77-3) → 3‑amino‑5,10‑dioxo‑1‑(2,4,5‑trimethoxyphenyl)‑5,10‑dihydro‑1H‑pyrazolo[1,2‑b]phthalazine‑2‑carbonitrile

Conditions	Yield
With hydrazine hydrate In water at 60℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Green chemistry;	95%

cycl-isopropylidene malonate (2033-24-1) + asaraldehyde (4460-86-0) → 5-(2,4,5-trimethoxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (117646-11-4)

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Ambient temperature;	94%
In methanol at 20℃; for 6h;	46%
In methanol at 20℃; Knoevenagel condensation;
In N,N-dimethyl-formamide

asaraldehyde (4460-86-0) + methyl 2-naphthyl ketone (93-08-3) → (2E)-1-(2-naphthyl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one (41343-22-0)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h;	94%
With potassium hydroxide In methanol at 20℃; for 24h;

asaraldehyde (4460-86-0) + para-bromoacetophenone (99-90-1) → 1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (941607-52-9)

Conditions	Yield
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation;	94%
With sodium hydroxide In ethanol for 2h;

asaraldehyde (4460-86-0) + 1-(4-methoxyphenyl)ethanone (100-06-1) → (E)-1-(4-methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (1003377-77-2)

Conditions	Yield
Stage #1: 1-(4-methoxyphenyl)ethanone With sodium hydroxide In ethanol; water at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Stage #2: asaraldehyde at 20℃; Claisen-Schmidt Condensation;	94%
With lithium hydroxide monohydrate In ethanol at 20℃; for 15h; Claisen-Schmidt Condensation;	92%
With lithium hydroxide monohydrate In ethanol at 20℃; for 15h; Claisen-Schmidt Condensation;	92%

N-hydroxyphthalimide (524-38-9) + asaraldehyde (4460-86-0) → 1,3-dioxoisoindolin-2-yl 2,4,5-trimethoxybenzoate (1441984-87-7)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In decane; ethyl acetate at 20 - 70℃; for 8h;	94%

Upstream product

• 5273-86-9 C₁₂H₁₆O₃ 
• 494-40-6 asarone 
• 60-29-7 diethyl ether 
• 586-96-9 Nitrosobenzene 
• 2033-89-8 3,4-dimethoxyphenol 
• 17598-03-7 5-ethenyl-1,2,4-trimethoxybenzene 
• 6906-65-6 1-propyl-2,4,5-trimethoxybenzene 
• 14977-61-8 chromyl chloride 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 68-12-2 N,N-dimethyl-formamide 
• 5353-15-1 1-allyl-2,4,5-trimethoxybenzene 
• 67-56-1 methanol 
• 2883-98-9 α-asarone 
• 29865-97-2 2,5-dihydroxy-4-methoxy-benzaldehyde 

Downstream Products

• 24160-53-0 2,4,5-trimethoxycinnamic acid 
• 73490-49-0 (E)-3-(2,4,5-trimethoxyphenyl)prop-2-enoic acid 
• 494-40-6 asarone 
• 207556-13-6 2-methyl-3-(2,4,5-trimethoxy-phenyl)-acrylic acid 
• 14600-17-0 2-cyano-3-(2,4,5-trimethoxy-phenyl)-acrylic acid ethyl ester 
• 148775-26-2 (E)-4-(2',4',5'-trimethoxyphenyl)but-3-en-2-one 
• 866999-53-3 (2.4.5-Trimethoxy-phenyl)-α-naphthyl-carbinol 
• 88775-43-3 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 5556-89-8 2,4,5-trimethoxybenzylidene propanedinitrile 
• 490-64-2 asaronic acid 
• 20491-91-2 2,4,5-trimethoxyphenol 

Relevant articles and documents

Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light

Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane

Difluoro(phenylsulfanyl)methane (PhSCF 2 H) was found to undergo a reaction with aromatic compounds mediated by SnCl 4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S, S ′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.