613-45-6

Basic information

• Product Name: 2,4-Dimethoxybenzaldehyde
• Synonyms: LABOTEST-BB LT00928518;2 4-DIMETHOXYBENZALDEHYDE 98% (GC);2,4-Dimethoxy;Benzaldehyde, 2,4-dimethoxy-;β-resorcylaldehyde dimethyl ether;NSC 27023;2,4-Bis(methyloxy)benzaldehyde;2,4-Dimethoxybenzaldehyde,98%
• CAS NO: 613-45-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 210-342-4
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aromatics;Aldehydes;C9;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 613-45-6.mol
• Article Data: 128

Chemical Properties

• Melting Point: 67-69 °C(lit.)
• Boiling Point: 165 °C10 mm Hg(lit.)
• Flash Point: 165°C/10mm
• Appearance: White to slightly brown/Fine Crystalline Powder
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.00071mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 607989
• CAS DataBase Reference: 2,4-Dimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethoxybenzaldehyde(613-45-6)
• EPA Substance Registry System: 2,4-Dimethoxybenzaldehyde(613-45-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 613-45-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 613-45-6 differently. You can refer to the following data:
1. A component of hair dyes
2. 2,4-Dimethoxybenzaldehyde is used as a reagent to specifically quantify phlorotannins. It is also used as a component of hair dyes.

Synthesis Reference(s)

Synthesis, p. 166, 1984 DOI: 10.1055/s-1984-30768

InChI:InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)9(5-8)12-2/h3-6H,1-2H3

Synthetic route

2,4-dimethoxylbenzyl alcohol (7314-44-5) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0333333h; Microwave irradiation;	100%
With C6H4MoNO7(1-)*C19H42N(1+); oxygen In water at 100℃; for 18h; Green chemistry; chemoselective reaction;	98%
With Merrifield's resin-bound N-aminoimidazolium chlorochromate In dichloromethane for 6.3h; Heating;	97%

C10H13N3O3 → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With caro's acid; silica gel In dichloromethane for 0.0833333h; Heating;	100%

2,4-Dihydroxybenzaldehyde (95-01-2) + methyl iodide (74-88-4) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With potassium carbonate In acetone Heating;	99%
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 3.5h;	95%
With potassium carbonate In acetone for 2.5h; Reflux;	94%

2,4-dimethoxybenzaldehyde semicarbazone (3030-94-2) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;	98%
With potassium permanganate; montmorillonite K-10 for 0.25h;	96%
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 0.5h; oxidative cleavage;	90%
With tribromo-isocyanuric acid In acetonitrile at 20℃; for 4h;	78%

2-(2',4'-dimethoxyphenyl)-1,3-dithiane (135655-77-5) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
Stage #1: 2-[2',4'-dimethoxyphenyl]-1,3-dithiane With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h; Stage #2: With water In dichloromethane at 0 - 20℃; for 0.5h;	97%

2,4-dimethoxybenzaldehyde phenylhydrazone (24575-92-6) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With potassium permanganate; montmorillonite K-10 for 0.25h;	96%

2,4-dimethoxybenzyl phenylacetate (258876-09-4) → phenylacetic acid (103-82-2) + 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 18h; Ambient temperature; Yields of byproduct given;	A 95% B n/a

2-(2,4-dimethoxy-phenyl)-[1,3]oxathiolane → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
Stage #1: 2-(2,4-dimethoxy-phenyl)-[1,3]oxathiolane With acetyl chloride; sodium nitrite In dichloromethane at 0 - 5℃; for 0.25h; Stage #2: With water In dichloromethane at 0 - 20℃; for 0.25h;	95%
With ammonium bromide; dihydrogen peroxide; vanadia In dichloromethane at 0 - 5℃; for 1.25h;	85%
With perchloric acid; dihydrogen peroxide; ammonium bromide; molybdic acid In dichloromethane at 0 - 5℃; for 2.5h;	80%

2,4-dimethoxyphenylacetic acid (6496-89-5) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;	95%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.25h; Microwave irradiation;	88%

2,4-dimethoxybenzaldoxime (31874-34-7) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With silica gel; iron(III) chloride for 0.00833333h; microwave irradiation;	93%
With (Bu4N)2S2O8 In 1,2-dichloro-ethane for 1h; Heating;	91.8%
With pyridinium chlorochromate at 20℃; for 4.5h;	90%

2,4-dimethoxylbenzyl alcohol (7314-44-5) + methyllithium (917-54-4) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With oxygen; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(I) bromide dimethylsulfide complex; bis(3-(perfluorooctyl)butyl)-2,2'-bipyridine In chlorobenzene at 90℃; for 3h; Oxidation;	93%

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + methyl iodide (74-88-4) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 18h;	93%

2,4-dimethoxybenzaldehyde dimethylacetal (91352-76-0) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With aluminum oxide; Oxone for 0.025h; Hydrolysis; Microwave irradiation;	92%

2-(2,4-dimethoxy-benzyloxy)-tetrahydro-pyran → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.233333h;	92%

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) → 2,4-dimethoxybenzonitrile (4107-65-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) + (2,4-Dimethoxy-benzyl)-[1-(2,4-dimethoxy-phenyl)-meth-(E)-ylidene]-amine

Conditions	Yield
With sodium hydroxide; sodium hypochlorite In ethanol for 0.25h; Ambient temperature;	A 89% B n/a C n/a

Decanoic acid 2,4-dimethoxy-benzyl ester (83026-07-7) → 1-decanoic acid (334-48-5) + tri(p-bromophenyl)amine (4316-58-9) + 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With 2,6-dimethylpyridine; 2a-radical-kation In water; acetonitrile oxidative electrolysis; Yield given;	A 86% B n/a C n/a

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 1,3-Dimethoxybenzene (151-10-0) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With silica gel; trichlorophosphate for 0.025h; Formylation; Microwave irradiation (300 W);	85%
With trichlorophosphate
With sodium hydroxide; pyrophosphoryl chloride 1) 100 deg C, 4 h; Yield given. Multistep reaction;

1-(bis(ethylthio)methyl)-2,4-dimethoxybenzene (114478-87-4) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With cetyl(trimethyl)-ammonium tribromide In dichloromethane at 0 - 5℃; for 0.0833333h;	85%
With ammonium heptamolybdate; dihydrogen peroxide; ammonium bromide; perchloric acid In dichloromethane; water at 0 - 5℃; for 0.5h;	82%

1,3-Dimethoxybenzene (151-10-0) + tris(diformylamino)methane (332047-72-0) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With trifluorormethanesulfonic acid In nitromethane at 20℃; for 2.5h;	84%
With aluminium trichloride In 1,2-dichloro-ethane at 2℃; for 15h;	45%
Stage #1: 1,3-Dimethoxybenzene; tris(diformylamino)methane With aluminium trichloride In 1,2-dichloro-ethane at -13 - 2℃; for 15h; Stage #2: With water	45%
With aluminium trichloride In 1,2-dichloro-ethane at -13 - 2℃; for 15h;	45%

1-iodo-2,4-dimethoxybenzene (20469-63-0) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; for 18h; Sealed tube; Glovebox; Inert atmosphere;	84%

N-methyl-N-phenylformamide (93-61-8) + 1,3-Dimethoxybenzene (151-10-0) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With trichlorophosphate In various solvent(s) at 100℃; for 1h; Vilsmeier formylation;	83%
With trichlorophosphate

2,4 dimethoxybenzoic acid (91-52-1) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation; Glovebox;	81%

2,4-dimethoxystyrene (40243-84-3) → formaldehyd (50-00-0) + 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 20℃; under 760.051 Torr; for 5h;	A n/a B 80%

difluoromethyl phenyl sulfide (1535-67-7) + 1,3-Dimethoxybenzene (151-10-0) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
Stage #1: difluoromethyl phenyl sulfide; 1,3-Dimethoxybenzene 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 water; dimethyl sulfoxide at 20℃; for 2h;	78%

cis-3-benzyloxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-methoxycarbonyl-2-azetidinone (83169-55-5, 84187-45-1, 88792-18-1, 88792-19-2, 90192-18-0, 97591-37-2) → 2,4 dimethoxybenzoic acid (91-52-1) + cis-4-(methoxycarbonyl)-2-oxo-3-<<(phenylmethoxy)carbonyl>amino>-1-azetidine (80542-47-8) + cis-3-benzyloxycarbonylamino-1-(2,4-dimethoxybenzoyl)-4-methoxycarbonyl-2-azetidinone (92973-54-1) + 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With dipotassium hydrogenphosphate; dipotassium peroxodisulfate In water; acetonitrile for 2h; Heating;	A 68 mg B 62% C 4.5% D 75%

2,4-dimethoxy-phenethyl alcohol (13398-65-7) → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With molecular sieve; pyridinium chlorochromate In dichloromethane at 20℃; for 8h;	73%

N-(2,4-dinitrophenyl)-N'-(2',4'-dimethoxybenzylidene)hydrazone → 2,4-Dimethoxybenzaldehyde (613-45-6)

Conditions	Yield
With potassium permanganate at 40℃; for 4.2h; Ionic liquid; chemoselective reaction;	69%

Dichloromethyl methyl ether (4885-02-3) + 1,3-Dimethoxybenzene (151-10-0) → 2,4-Dimethoxybenzaldehyde (613-45-6) + 2,6-dimethoxybenzaldehyde (3392-97-0)

Conditions	Yield
Stage #1: 1,3-Dimethoxybenzene With titanium tetrachloride In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: Dichloromethyl methyl ether In dichloromethane at 0℃; for 0.75h; Inert atmosphere; Overall yield = 79 %;	A 61% B 18%

1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (36685-67-3, 84426-23-3)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h; Claisen-Schmidt Condensation;	100%
With sodium hydroxide In ethanol at 20℃; for 16h;	94%
With potassium hydroxide In ethanol at 20℃; Claisen Schmidt condensation;	90%

2,4-Dimethoxybenzaldehyde (613-45-6) → 2,4-dimethoxyphenol (13330-65-9)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In methanol; water at 20℃; for 20h;	100%
With sulfuric acid; dihydrogen peroxide In methanol at 20℃; for 20h;	94%
With dihydrogen peroxide; sulfuric acid In methanol for 14h; Ambient temperature;	90%

glycine ethyl ester hydrochloride (623-33-6) + 2,4-Dimethoxybenzaldehyde (613-45-6) → ethyl 2-{[(2,4-dimethoxyphenyl)methyl]amino}acetate (95218-34-1)

Conditions	Yield
With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane for 17h;	100%
With sodium tetrahydroborate; triethylamine In methanol; ethanol for 1h; Ambient temperature;	59%
Stage #1: glycine ethyl ester hydrochloride; 2,4-Dimethoxybenzaldehyde With triethylamine In acetonitrile at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 18h; Inert atmosphere;	49%
Stage #1: glycine ethyl ester hydrochloride; 2,4-Dimethoxybenzaldehyde With triethylamine In 1,1-dichloroethane for 1h; Stage #2: With water; sodium tris(acetoxy)borohydride In 1,1-dichloroethane for 72h; Stage #3: With sodium hydrogencarbonate In 1,1-dichloroethane; water

2,4-Dimethoxybenzaldehyde (613-45-6) → 2,4-dimethoxylbenzyl alcohol (7314-44-5)

Conditions	Yield
With tri-n-butyl-tin hydride; phenylboronic acid In dichloromethane at 20℃; for 16h;	100%
With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;	100%
With water; nickel dichloride; zinc In N,N-dimethyl-formamide for 1.5h; Ambient temperature;	98%

3-acetyl-2,4-dihydroxyquinoline (26138-64-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-1-(2,4-Dihydroxy-quinolin-3-yl)-3-(2,4-dimethoxy-phenyl)-propenone

Conditions	Yield
	100%

4-methoxy-aniline (104-94-9) + 2,4-Dimethoxybenzaldehyde (613-45-6) → N-(2,4-dimethoxybenzylidene)-4-methoxyaniline (123794-61-6)

Conditions	Yield
In toluene for 40h; Heating;	100%
In toluene at 165℃; for 18h;
In chlorobenzene for 1h; Reflux;

1.3-propanedithiol (109-80-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 2-(2',4'-dimethoxyphenyl)-1,3-dithiane (135655-77-5)

Conditions	Yield
With Lewis acid	100%
With acetyl chloride at 20℃; for 0.0666667h;	98%
With nickel dichloride In methanol; dichloromethane at 20℃; for 0.2h;	96%

2,4-Dimethoxybenzaldehyde (613-45-6) + (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((E)-4,8-dimethyl-nona-3,7-dienyl)-5-methyl-dihydro-furan-2-one → (3R,4R,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[(2,4-dimethoxy-phenyl)-hydroxy-methyl]-5-((E)-4,8-dimethyl-nona-3,7-dienyl)-5-methyl-dihydro-furan-2-one

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;	100%

isopropyltriphenylphosphonium iodide (24470-78-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 2,4-dimethoxy-1-(2-methyl-propenyl)-benzene (798559-93-0)

Conditions	Yield
Stage #1: isopropyltriphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: 2,4-Dimethoxybenzaldehyde In tetrahydrofuran; hexane at 20℃; for 4h;	100%

2,4-Dimethoxybenzaldehyde (613-45-6) + methoxycarbonylmethylamine (616-34-2) → (2,4-dimethoxybenzylamino)acetic acid methyl ester (20839-81-0)

Conditions	Yield
With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane at 20℃; for 24h;	100%

2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-bis(2,4-dimethoxyphenyl)ethene

Conditions	Yield
With woollins’ reagent In toluene for 20h; Heating;	100%

2-(Methylthio)aniline (2987-53-3) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 2-methylthio-N-(2,4-dimethoxybenzylidene)aniline

Conditions	Yield
In toluene Heating;	100%

2,4-Dimethoxybenzaldehyde (613-45-6) + methylamine (74-89-5) → 1-(2,4-dimethoxyphenyl)-N-methylmethanamine (102503-23-1)

Conditions	Yield
With sodium tetrahydroborate In methanol for 2h;	100%
Stage #1: 2,4-Dimethoxybenzaldehyde; methylamine In methanol at 0 - 20℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 12h;	92%
Stage #1: 2,4-Dimethoxybenzaldehyde; methylamine In methanol at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 2℃; for 3h; Stage #3: With hydrogenchloride; water; sodium hydrogencarbonate more than 3 stages;	81%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 25℃;

2-aminophenylacetic acid methyl ester (35613-44-6) + 2,4-Dimethoxybenzaldehyde (613-45-6) → C18H19NO4 (1198328-58-3)

Conditions	Yield
In methanol at 20℃; for 16h; Inert atmosphere;	100%

2'-(propargyloxy)acetophenone (41580-73-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 3-(2,4-dimethoxy-phenyl)-1-(2-prop-2-ynyloxy-phenyl)-propenone (1227420-52-1)

Conditions	Yield
Stage #1: 2'-(propargyloxy)acetophenone With sodium hydroxide In methanol at 25℃; for 0.5h; Claisen-Schmidt condensation; Stage #2: 2,4-Dimethoxybenzaldehyde In methanol at 25℃; Claisen-Schmidt condensation;	100%

5-hydroxypentylamine (2508-29-4) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 5-((2,4-dimethoxybenzyl)amino)pentan-1-ol (932176-57-3)

Conditions	Yield
Stage #1: 5-hydroxypentylamine; 2,4-Dimethoxybenzaldehyde In toluene for 4h; Reflux; Dean-Stark; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 0.166667h;	100%
Stage #1: 5-hydroxypentylamine; 2,4-Dimethoxybenzaldehyde With acetic acid In methanol at 10℃; for 0.5h; Stage #2: With sodium tetrahydroborate In methanol at -10 - 10℃; for 1.66667h; Stage #3: With sodium hydrogencarbonate In methanol for 0.5h;

4-chloro-aniline (106-47-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 4-chloro-N-(2,4-dimethoxybenzylidene)aniline (38608-00-3)

Conditions	Yield
In toluene at 80℃; for 12h; Inert atmosphere;	100%

allylmagnesium bromide (2622-05-1) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 1-(2,4-dimethoxyphenyl)but-3-en-1-ol (1023294-87-2)

Conditions	Yield
In diethyl ether at 0 - 20℃;	100%
In tetrahydrofuran; diethyl ether at 0 - 20℃;

2,4-Dimethoxybenzaldehyde (613-45-6) + Cyclopentamine (1003-03-8) → N-cyclopentyl-N-(2,4-dimethoxybenzyl)amine (356092-74-5)

Conditions	Yield
Stage #1: 2,4-Dimethoxybenzaldehyde; Cyclopentamine In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol for 0.5h;	100%

4-(2-cyclohexylethoxy)-2-fluoroaniline + 2,4-Dimethoxybenzaldehyde (613-45-6) → 4-(2-cyclohexylethoxy)-N-(2,4-dimethoxybenzyl)-2-fluoroaniline

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃;	100%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 2,4-dimethoxybenzaldehyde O-benzyloxime

Conditions	Yield
With pyrrolidine In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent;	100%

N-methylpropargylamine (35161-71-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → N-(2,4-dimethoxybenzyl)-N-methylprop-2-yn-1-amine (56862-22-7)

Conditions	Yield
Stage #1: 2,4-Dimethoxybenzaldehyde With acetic acid In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: methyl(propargyl)amine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #3: With sodium tris(acetoxy)borohydride In dichloromethane at 0℃; Inert atmosphere;	100%

inden-1-one (83-33-0) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-2-(2,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With hydrogenchloride; acetic acid at 20℃; for 24h;	99.1%
basic condition;
Claisen-Schmidt Condensation; Alkaline conditions;

malonic acid (141-82-2) + 2,4-Dimethoxybenzaldehyde (613-45-6) → (E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid (16909-09-4)

Conditions	Yield
With piperidine; pyridine at 80 - 115℃; for 4h; Knoevenagel Condensation;	99%
With piperidine; pyridine at 125℃; for 3.5h;	98%
Stage #1: malonic acid; 2,4-Dimethoxybenzaldehyde With pyridine; 3-amino propanoic acid for 1.5h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In water at 0℃; Inert atmosphere;	90%

2,4-Dimethoxybenzaldehyde (613-45-6) + 1-(4-methoxyphenyl)ethanone (100-06-1) → (E)-3-(2,4-dimethoxyphenyl)-1-(4-methoxyphenyl)-2-propen-1-one (24533-49-1)

Conditions	Yield
Stage #1: 2,4-Dimethoxybenzaldehyde; 1-(4-methoxyphenyl)ethanone With potassium hydroxide In ethanol; water at 20℃; for 12h; Claisen Schmidt condensation; Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4;	99%
With sodium hydroxide In ethanol; water at 0 - 20℃; for 12h; Claisen-Schmidt Condensation;	98%
With sodium hydroxide In ethanol; water at 0 - 20℃; for 15h; Claisen-Schmidt Condensation;	41%

2,4-Dimethoxybenzylamine (20781-20-8) + 2,4-Dimethoxybenzaldehyde (613-45-6) → bis(2,4-dimethoxybenzyl)amine (20781-23-1)

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃;	99%
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 2h;	92%
(i) TsOH, toluene, (ii) aq. NaBH4; Multistep reaction;
Stage #1: 2,4-Dimethoxybenzylamine; 2,4-Dimethoxybenzaldehyde In ethanol at 20℃; for 2h; Stage #2: With sodium tris(acetoxy)borohydride In ethanol at 20℃; for 1h;	8 g
Stage #1: 2,4-Dimethoxybenzylamine; 2,4-Dimethoxybenzaldehyde In methanol at 20℃; for 1h; Stage #2: With methanol; sodium tetrahydroborate at 20℃;

N-(3-Chloro-phenyl)-2-hydrazono-N'-hydroxy-propionamidine (85914-42-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → N-(3-Chloro-phenyl)-2-{[1-(2,4-dimethoxy-phenyl)-meth-(Z)-ylidene]-hydrazono}-N'-hydroxy-propionamidine (126389-68-2)

Conditions	Yield
In ethanol 1.) reflux, 2 to 5 min, 2.) RT;	99%

2,4-Dimethoxybenzaldehyde (613-45-6) + 5-phenylfuran-2,3-dione (55991-67-8) → 2-(2,4-Dimethoxy-phenyl)-6-phenyl-[1,3]dioxin-4-one (77092-04-7)

Conditions	Yield
In benzene for 3h; Heating;	99%

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 151-10-0 1,3-Dimethoxybenzene 
• 77-78-1 dimethyl sulfate 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 93-61-8 N-methyl-N-phenylformamide 
• 1899-02-1 trimethylphenylammonium hydroxide 
• 617-84-5 N-formyldiethylamine 
• 74-90-8 hydrogen cyanide 
• 103-70-8 Formanilid 
• 186581-53-3 diazomethane 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 7314-44-5 2,4-dimethoxylbenzyl alcohol 
• 83026-07-7 Decanoic acid 2,4-dimethoxy-benzyl ester 
• 83169-55-5 cis-3-benzyloxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-methoxycarbonyl-2-azetidinone 

Downstream Products

• 103386-15-8 1-(2,4-dimethoxybenzyl)piperidine 
• 99988-44-0 5-[(2,4-dimethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one 
• 149246-08-2 N-[5-(2,4-dimethoxy-benzylidene)-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl]-acetamide 
• 36752-68-8 (Z)-2-(2,4-dimethoxybenzylidene)benzofuran-3(2H)-one 
• 103399-84-4 4-[4-(2,4-dimethoxy-benzyliden)-3-octadecylamino-5-oxo-4,5-dihydro-pyrazol-1-yl]-benzenesulfonic acid 
• 42172-51-0 (2Z)-3-(2’,4’-dimethoxyphenyl)-2-phenylacrylonitrile 
• 15804-78-1 1-(2,4-Dimethoxyphenyl)-2-nitropropen 
• 42174-73-2 (E)-2,4-dimethoxycinnamic acid ethyl ester 
• 121365-35-3 6t-(2,4-dimethoxy-phenyl)-4-oxo-hex-5-enoic acid 
• 79004-62-9 1,3-bis-(2,4-dimethoxyphenyl)propenone 
• 25163-69-3 2,2',4,4',6'-pentamethoxychalcone 
• 25163-69-3 2,4,2',4',6'-pentamethoxy-trans-chalcone 
• 13388-83-5 2,4-Dimethoxy-benzylidenamino-acetaldehyd-diethylacetal 
• 102616-66-0 6-((2,4-dimethoxyphenyl)-4-morpholinylmethyl)-1,3-benzodioxol-5-ol 

Relevant articles and documents

Synthesis of 4-Methoxysalicylaldehyde via selective monomethylation of 2,4-dihydroxybenzaldehyde

4-Methoxysalicylaldehyde, a naturally occurring product, has a range of industrial applications in the preparation of organic compounds, drugs and therapeutic agents. 4-Methoxysalicylaldehyde can be synthesised via selective monomethylation of 2,4-dihydroxybenzaldehyde in toluene in the presence of NaHCO3 in higher yield using cheaper reagents with little production of dimethylation product compared to previous methods. The location of the methoxyl group was confirmed by conversion to 3-acetyl-7-methoxycoumarin by condensation with ethyl acetoacetate.

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Unexpectedly ambivalent O2 role in the autocatalytic photooxidation of 2-methoxybenzyl alcohol in water

Abstract An unusual autocatalytic photooxidation of 2-methoxybenzyl alcohol has been observed under UV irradiation in aqueous medium. The homogeneous oxidation is catalyzed by the corresponding aldehyde that is also the main oxidation product. The trend of alcohol disappearance rate matches the typical shape of an autocatalytic process, where a crucial and ambivalent role is played by the presence of molecular oxygen. Low oxygen concentrations give rise to a zero-order reaction since the beginning of irradiation, while higher amounts of oxygen reduce the alcohol oxidation rate until the aldehyde reaches a concentration high enough to speed up the alcohol's conversion. Experiments performed by varying alcohol, aldehyde and oxygen concentrations in both aqueous and organic media suggest that the alcohol oxidation is initially favored by the presence of oxygen. Once the formed aldehyde competes for photon absorption, the oxidation is driven by aldehydes alpha cleavage leading to reactive oxygenated species in aqueous medium. An excess of oxygen quenches the latter processes thus inhibiting/slowing down the reaction.

Fe Doped MIL-101/Graphene Nanohybrid for Photocatalytic Oxidation of Alcohols Under Visible-Light Irradiation

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