7311-34-4

Basic information

• Product Name: 3,5-Dimethoxybenzaldehyde
• Synonyms: 311-34-4;Benzaldehyde, 3,5-dimiethoxy;3,5-DIMETHOXYBENZALDEHYDE;BENZALDEHYDE, 3,5-DIMETHOXY-;3,5-Dimethoxybenzeldehyde;3,5-Dimethoxybenzaldehye;3,5-Dimethoxybenzaldehyde 98%;3,5-Dimethoxybenzaldehyde ,98%
• CAS NO: 7311-34-4
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 230-772-6
• Product Categories: Carbonyl Compounds;Aromatic Aldehydes & Derivatives (substituted);Adehydes, Acetals & Ketones;Anisoles, Alkyloxy Compounds & Phenylacetates;Building Blocks for Dendrimers;Functional Materials;Aldehydes;C9;Carbonyl Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 7311-34-4.mol
• Article Data: 102

Chemical Properties

• Melting Point: 45-48 °C(lit.)
• Boiling Point: 151 °C16 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to beige/Crystalline Solid
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.00478mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 2042374
• CAS DataBase Reference: 3,5-Dimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethoxybenzaldehyde(7311-34-4)
• EPA Substance Registry System: 3,5-Dimethoxybenzaldehyde(7311-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 7311-34-4(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline solid

Uses

Different sources of media describe the Uses of 7311-34-4 differently. You can refer to the following data:
1. 3,5-Dimethoxybenzaldehyde is used frequently as synthetic building block. 3,5-Dimethoxybenzaldehyde, is a benzaldehyde derivative, that can be used as a building block in the synthesis of more complex structures.
2. 3,5-Dimethoxybenzaldehyde is used as a building block in organic synthesis. It is used to prepare isomeric hyperbranched polyetherketones.

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

Synthetic route

3,5-dimethoxybenzaldoxime (34967-25-4) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.25h; Oxidation; Heating;	100%
With 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride In water at 50℃; for 0.333333h; pH=7;	85%
With quinolinium chlorochromate(VI) for 0.583333h;	50%

3,5-dimethoxybenzyl alcohol (705-76-0) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	99.5%
With 1,2-dimethyl-3-[6-(methylsulfinyl)hexyl]-1H-imidazolium triflate; oxalyl dichloride; triethylamine In dichloromethane; acetonitrile at -78 - 20℃; Swern oxidation;	97%
With Dess-Martin periodane In dichloromethane at 0℃; Inert atmosphere;	96%

3,5-dihydroxybenzaldehyde (26153-38-8) + methyl iodide (74-88-4) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	99%
With potassium carbonate In acetone at 80℃; for 12h; Inert atmosphere; Schlenk technique;	92%
With potassium carbonate In acetone Heating;	90%
Stage #1: 3,5-dihydroxybenzaldehyde With potassium carbonate In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In acetone for 6h; Reflux; Inert atmosphere;	69.4%

2-bromo-3,5-dimethoxybenzyl alcohol (74726-76-4) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
Stage #1: 2-bromo-3,5-dimethoxybenzyl alcohol With water; lead(IV) tetraacetate; potassium nitrate at 37℃; for 1.5h; Stage #2: With rhenium(IV) sulfide at 45℃; for 2h; Temperature;	98.5%

(3,5-dimethoxyphenyl)acetic acid (4670-10-4) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;	96%
With dipotassium peroxodisulfate In water at 90℃; for 12h; Green chemistry;	62%

1,3-dimethoxy-5-methylbenzene (4179-19-5) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;	95%
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 1 h / 25 °C / Inert atmosphere 2: hexamethylenetetramine / water / 12 h / 120 °C / Inert atmosphere View Scheme

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere;	87%

(3aR,5R,6S,6aR)-6-(3,5-Dimethoxy-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole → 3,5-dimethoxybenzaldehdye (7311-34-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 2.5h; Ambient temperature;	A n/a B 86%

1-[(1R,2S)-4-Benzyloxy-1-ethyl-2-(4-methoxy-benzyloxymethyl)-butoxymethyl]-3,5-dimethoxy-benzene → 3,5-dimethoxybenzaldehdye (7311-34-4) + (3R,4S)-6-Benzyloxy-4-(4-methoxy-benzyloxymethyl)-hexan-3-ol (96016-38-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; Petroleum ether at 5℃; for 0.08h;	A n/a B 86%

1-((1R,2S,3S)-2,4-Bis-benzyloxy-1,3-dimethyl-butoxymethyl)-3,5-dimethoxy-benzene → 3,5-dimethoxybenzaldehdye (7311-34-4) + (2R,3S,4S)-3,5-Bis-benzyloxy-4-methyl-pentan-2-ol (96016-18-1)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 0.25h; Ambient temperature;	A n/a B 85%

1,3-Dimethoxy-5-[(1R,2R,3R)-3-(4-methoxy-benzyloxy)-2,4-bis-methoxymethoxy-1-methyl-butoxymethyl]-benzene → 3,5-dimethoxybenzaldehdye (7311-34-4) + 4-methoxy-benzaldehyde (123-11-5) + (2R,3S,4R)-4-(3,5-Dimethoxy-benzyloxy)-1,3-bis-methoxymethoxy-pentan-2-ol + (2R,3R,4R)-4-(4-Methoxy-benzyloxy)-3,5-bis-methoxymethoxy-pentan-2-ol (96016-37-4, 107297-50-7)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; Petroleum ether at 5℃; for 0.6h;	A n/a B n/a C 4% D 80%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; Petroleum ether at 5℃; for 0.6h;	A n/a B n/a C 4% D 4%

1-bromo-3,5-dimethoxybenzene (20469-65-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
Stage #1: 1-bromo-3,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane for 0.333333h; Inert atmosphere; Cooling; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane for 0.333333h; Cooling; Inert atmosphere;	78%

formic acid (64-18-6) + 1-iodo-3,5-dimethoxybenzene (25245-27-6) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;	77%

1-(azidomethyl)-3,5-dimethoxybenzene (712329-47-0) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
Stage #1: 1-(azidomethyl)-3,5-dimethoxybenzene With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere; Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere;	76%

1-[(2R,3R)-2-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methoxymethoxy-butoxymethyl]-3,5-dimethoxy-benzene → 3,5-dimethoxybenzaldehdye (7311-34-4) + 4-methoxy-benzaldehyde (123-11-5) + (2R,3R)-3-Benzyloxy-4-(3,5-dimethoxy-benzyloxy)-2-methoxymethoxy-butan-1-ol + (2R,3R)-2-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methoxymethoxy-butan-1-ol (96016-36-3)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 5℃; for 1.8h;	A n/a B n/a C 6.5% D 75%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 5℃; for 1.8h;	A n/a B n/a C 6.5% D 6.5%

C18H22O5 → 3,5-dimethoxybenzaldehdye (7311-34-4) + 4-methoxy-benzaldehyde (123-11-5)

Conditions	Yield
With quinoline; (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; oxygen In 1,4-dioxane at 100℃; under 760.051 Torr; for 24h;	A 74% B 61%

3,5,4'-trimethoxy-trans-stilbene (22255-22-7) → 3,5-dimethoxybenzaldehdye (7311-34-4) + 4-methoxy-benzaldehyde (123-11-5)

Conditions	Yield
Stage #1: 3,5,4'-trimethoxy-trans-stilbene With ozone In methanol; dichloromethane at -78℃; Stage #2: With triphenylphosphine In methanol; dichloromethane for 0.5h;	A 60% B 73%

3,5-dimethoxybenzoyl chloride (17213-57-9) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With hydrogen; sodium acetate; palladium on activated charcoal under 2427.2 Torr; 1h, then 60 degC, overnight;	70%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;	60%
With Pd-BaSO4; xylene at 140℃; Hydrogenation;

formaldehyd (50-00-0) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → 3,5-dimethoxybenzaldehdye (7311-34-4)

Conditions	Yield
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave;	70%

C18H22O5 → 3,5-dimethoxybenzaldehdye (7311-34-4) + 4-methoxy-benzaldehyde (123-11-5)

Conditions	Yield
With quinoline; (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; oxygen In 1,4-dioxane at 100℃; under 760.051 Torr; for 24h;	A 70% B 67%

(4S,5R)-4-(3,5-Dimethoxy-benzyloxymethyl)-5-ethyl-2-(4-methoxy-phenyl)-4-methyl-[1,3]dioxolane → 3,5-dimethoxybenzaldehdye (7311-34-4) + [(4S,5R)-5-Ethyl-2-(4-methoxy-phenyl)-4-methyl-[1,3]dioxolan-4-yl]-methanol (96016-44-3, 107297-53-0) + 4-Methoxy-benzoic acid (1R,2S)-1-ethyl-2,3-dihydroxy-2-methyl-propyl ester (96016-45-4)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; Petroleum ether at 10℃; for 1h;	A n/a B 66% C 5.5%

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxybenzyl alcohol (705-76-0)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h;	100%
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h; Inert atmosphere;	100%

2-Phenyl-[1,3]dithiane (5425-44-5) + 3,5-dimethoxybenzaldehdye (7311-34-4) → (3,5-dimethoxyphenyl)(2-phenyl-[1,3]-dithian-2-yl)-methanol (92989-59-8)

Conditions	Yield
Stage #1: 2-Phenyl-[1,3]dithiane With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 0 - 20℃; for 1.5h; Further stages.;	100%
Stage #1: 2-Phenyl-[1,3]dithiane With n-butyllithium In tetrahydrofuran at 0℃; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 0 - 20℃; for 1.5h;	100%
Stage #1: 2-Phenyl-[1,3]dithiane With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; Inert atmosphere; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran; cyclohexane at -78 - 20℃; Inert atmosphere;	90%

carbon tetrabromide (558-13-4) + 3,5-dimethoxybenzaldehdye (7311-34-4) → 1-(2,2-dibromoethen-1-yl)-3,5-dimethoxybenzene (205746-51-6)

Conditions	Yield
With triphenylphosphine In dichloromethane at 0℃; for 2h; Inert atmosphere;	100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 3,5-dimethoxybenzaldehdye In dichloromethane Inert atmosphere; Schlenk technique;	97%
With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h;	96.4%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 3,5-dimethoxybenzaldehdye (7311-34-4) → 3-(3,5-dimethoxyphenyl)acrylonitrile (153507-02-9)

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 20℃; for 17h;	100%
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at 28℃;

pyrrolidine (123-75-1) + trimethylsilyl cyanide (7677-24-9) + 3,5-dimethoxybenzaldehdye (7311-34-4) → 2-(3,5-dimethoxyphenyl)-2-(pyrrolidin-1-yl)acetonitrile (1108730-66-0)

Conditions	Yield
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.5h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	100%

trimethylsilyl cyanide (7677-24-9) + 3,5-dimethoxybenzaldehdye (7311-34-4) + 3-Phenylpropan-1-amine (2038-57-5) → 2-(3,5-dimethoxyphenyl)-2-(3-phenylpropylamino)acetonitrile (1108730-65-9)

Conditions	Yield
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	100%

3,5-dimethoxybenzaldehdye (7311-34-4) + trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9) → (Z)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(3,5-dimethoxyphenyl)acrylate (1259394-66-5)

Conditions	Yield
With caesium carbonate for 7h; Horner-Wadsworth-Emmons olefination; neat (no solvent, solid phase); stereoselective reaction;	100%

t-butoxycarbonylhydrazine (870-46-2) + 3,5-dimethoxybenzaldehdye (7311-34-4) → (E)-tert-butyl 2-(3,5-dimethoxybenzylidene)hydrazinecarboxylate (106728-65-8)

Conditions	Yield
at 20℃; for 1h; Neat (no solvent); Ball-milling;	100%

3,5-dimethoxybenzaldehdye (7311-34-4) + benzoic acid hydrazide (613-94-5) → (E)-N'-(3,5-dimethoxybenzylidene)benzohydrazide (678536-02-2)

Conditions	Yield
at 20℃; for 2h; Neat (no solvent); Ball-milling;	100%
In ethanol Reflux;

3,5-dimethoxybenzaldehdye (7311-34-4) + toluene-4-sulfonic acid hydrazide (1576-35-8) → (E)-N′-(3,5-dimethoxybenzylidene)-4-methylbenzenesulfonohydrazide (1338091-83-0)

Conditions	Yield
at 20℃; for 3h; Neat (no solvent); Ball-milling;	100%
In methanol at 60℃; for 0.0833333 - 1h;	95%

3,5-dimethoxybenzaldehdye (7311-34-4) + (4-(allyloxy)phenyl)methanamine (83171-41-9) → C19H21NO3

Conditions	Yield
In toluene for 20h; Reflux; Molecular sieve;	100%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3,5-dimethoxybenzaldehdye (7311-34-4) → ethyl 3,5-dimethoxycinnamate (29584-64-3, 42174-79-8)

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 20h; Horner-Wadsworth-Emmons reaction; Reflux;	100%
With sodium tert-pentoxide at 0 - 20℃; for 1h; Horner-Wadsworth-Emmons Olefination; Green chemistry;

3,5-dimethoxybenzaldehdye (7311-34-4) + ethane-1,2-dithiol (540-63-6) → 2-(3,5-dimethoxy-phenyl)-1,3-dithiolane (61571-96-8)

Conditions	Yield
With diethyl ether; boron trifluoride In dichloromethane for 15h;	99%
With amberlyst-15 In acetonitrile for 1h;	99.93%
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h;

1.3-propanedithiol (109-80-8) + 3,5-dimethoxybenzaldehdye (7311-34-4) → 2-(3,5-dimethoxy-phenyl)-1,3-dithiane (57009-72-0)

Conditions	Yield
With amberlyst-15 In acetonitrile for 1h;	99.91%
With nickel dichloride In methanol; dichloromethane at 20℃; Inert atmosphere;	90%
With hydrogenchloride In chloroform for 0.583333h;	78%
With hydrogenchloride In chloroform for 18h; Ambient temperature;	75.8%

3,5-dimethoxybenzaldehdye (7311-34-4) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-3-(3,5-dimethoxy-phenyl)-acrylic acid ethyl ester

Conditions	Yield
With piperazine In acetonitrile for 1h; Knoevenagel condensation; electroosmos;	99.9%

trimethylsilyl cyanide (7677-24-9) + 3,5-dimethoxybenzaldehdye (7311-34-4) + phenethylamine (64-04-0) → 2-(3,5-dimethoxyphenyl)-2-(phenethylamino)acetonitrile (1108730-64-8)

Conditions	Yield
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	99.9%

trimethylsilyl cyanide (7677-24-9) + 3,5-dimethoxybenzaldehdye (7311-34-4) + benzylamine (100-46-9) → 2-(benzylamino)-2-(3,5-dimethoxyphenyl)acetonitrile

Conditions	Yield
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	99.9%

3,5-dimethoxybenzaldehdye (7311-34-4) + ethyl 2-cyanoacetate (105-56-6) → 3-(3,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester (5864-90-4)

Conditions	Yield
With 3-(1-piperazino)propyl functionalised silica gel In acetonitrile Knoevenagel condensation;	99.5%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 5h; Knoevenagel Condensation;	90%
With piperidine In ethanol at 20℃;
With sodium hydroxide In ethanol for 0.25h; air atmosphere;
With piperazine immobilized by 4-benzyl spacer on silica gel In acetonitrile at 20℃; for 0.0833333h; Knoevenagel Condensation; Flow reactor;

3,5-dimethoxybenzaldehdye (7311-34-4) + ethyl 2-cyanoacetate (105-56-6) → 3-(3,5-dimethoxyphenyl)-2-cyano acrylic acid ethyl ester (5864-90-4)

Conditions	Yield
With 3-(1-piperazino)propyl-functionalised silica gel In acetonitrile Knoevenagel reaction; electroosmotic flow;	99.5%

3,5-dimethoxybenzaldehdye (7311-34-4) + (4-nitrophenyl)ethanone (100-19-6) → C17H15NO5

Conditions	Yield
Stage #1: (4-nitrophenyl)ethanone With lithium hydroxide monohydrate In methanol at 20℃; for 1h; Stage #2: 3,5-dimethoxybenzaldehdye In methanol at 20℃; for 3h;	99.5%

3,5-dimethoxybenzaldehdye (7311-34-4) + trimethyl orthoformate (149-73-5) → 3,5-dimethoxybenzaldehyde dimethyl acetal (59276-34-5)

Conditions	Yield
With amberlyst-15 In acetonitrile for 1h; electroosmos;	99.4%
With amberlyst-15 In acetonitrile for 0.166667h;	98.4%
With ammonium chloride In methanol for 24h;	98%
With toluene-4-sulfonic acid

3,5-dimethoxybenzaldehdye (7311-34-4) + malononitrile (109-77-3) → β,β-dicyano-3,5-dimethoxystyrene (26495-19-2)

Conditions	Yield
With 3-(1-piperazino)propyl functionalised silica gel In acetonitrile Knoevenagel condensation;	99.2%
With 3-(1-piperazino)propyl-functionalised silica gel In acetonitrile Knoevenagel reaction; electroosmotic flow;	99.2%
With piperazine In acetonitrile for 1h; Knoevenagel condensation; electroosmos;	99.2%

trimethylsilyl cyanide (7677-24-9) + 3,5-dimethoxybenzaldehdye (7311-34-4) → α-(3,5-dimethoxyphenyl)-α-(trimethylsilyloxy)acetonitrile (144758-83-8)

Conditions	Yield
With C32H39Br2MgN2(1-)*C16H32LiO4(1+) In chloroform-d1 at 20℃; for 3h; Inert atmosphere; Glovebox;	99%
With zinc(II) iodide In benzene for 1.5h; Ambient temperature;	93%
In acetonitrile at 45℃; for 4h;	89%

3,5-dimethoxybenzaldehdye (7311-34-4) + 2-tert-Butoxycarbonyl-1-methoxycarbonylethylidene(triphenyl)phosphorane (57367-56-3) → 2-[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester (115046-50-9)

Conditions	Yield
In benzene for 48h; Heating;	99%

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxybenzoic acid (1132-21-4)

Conditions	Yield
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	99%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	95%
With sodium perborate In acetic acid at 45 - 50℃; for 8h;	83%

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxy-benzonitrile (19179-31-8)

Conditions	Yield
With oxygen; copper; ammonium chloride In pyridine at 60℃; for 24h;	99%
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;	99%
With trimethylsilylazide; zirconium(IV) chloride In acetonitrile at 20℃; for 0.333333h;	69%
With ammonia; iodine In tetrahydrofuran; water at 20℃;

3,5-dimethoxybenzaldehdye (7311-34-4) + methyl-triphenylphosphonium iodide (2065-66-9) → 3,5-dimethoxystyrene (40243-87-6)

Conditions	Yield
Stage #1: methyl-triphenylphosphonium iodide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Wittig Olefination; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran; mineral oil at 0 - 20℃; for 10h; Wittig Olefination;	99%
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In diethyl ether at 20℃; for 2h; Wittig reaction; Stage #2: 3,5-dimethoxybenzaldehdye In diethyl ether at 0 - 20℃; Wittig reaction;	96%
With potassium tert-butylate In N,N-dimethyl-formamide at -75℃; for 4h; Inert atmosphere;	86%

3,5-dimethoxybenzaldehdye (7311-34-4) + Methyltriphenylphosphonium bromide (1779-49-3) → 3,5-dimethoxystyrene (40243-87-6)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	99%
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil for 1h; Wittig Olefination; Inert atmosphere; Reflux; Stage #2: 3,5-dimethoxybenzaldehdye In tetrahydrofuran; mineral oil for 2h; Wittig Olefination; Inert atmosphere; Reflux;	99%
With potassium tert-butylate In tetrahydrofuran at -70 - 20℃; for 2h; Wittig reaction;	96%

Upstream product

• 1132-21-4 3,5-dimethoxybenzoic acid 
• 10026-13-8 phosphorus pentachloride 
• 87282-04-0 3,5-dimethoxy-N-phenylbenzamide 
• 108-88-3 toluene 
• 1310742-35-8 1-(3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol 
• 90-05-1 2-methoxy-phenol 
• 712329-47-0 1-(azidomethyl)-3,5-dimethoxybenzene 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 59276-34-5 3,5-dimethoxybenzaldehyde dimethyl acetal 
• 59276-37-8 3,4,5-trimethoxybenzaldehyde dimethyl acetal 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 78916-49-1 1-phenyl-2-(3,5-dimethoxyphenyl)ethene 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 

Downstream Products

• 146205-98-3 (E)-1,3-dimethoxy-5-(prop-1-en-1-yl)benzene 
• 203912-55-4 1-(3,5-dimethoxy-phenyl)-propan-1-ol 
• 86802-81-5 2-<(3,5-dimethoxyphenyl)methyl>furan 
• 38228-28-3 1-(1-hydroxypentyl)-3,5-dimethoxybenzene 
• 135085-37-9 6-Benzyl-3-(3,5-dimethoxyphenyl)-s-triazolo<3,4-a>phthalazine 
• 95124-67-7 5-methyl-3-(3,5-dimethoxyphenyl)-1,2,4-oxadiazole 
• 19055-50-6 2-(3,5-Dimethoxy-phenyl)-1,3-indandion 
• 25458-10-0 2-{[1-(3,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-2-methyl-propan-1-ol 
• 129478-11-1 1-(3,5-dimethoxyphenyl)-1-heptanol 
• 5259-09-6 5-(1-hydroxytridecyl)-1,3-dimethoxybenzene 
• 412925-58-7 3-Amino-3-(3,5-dimethoxy-phenyl)-propionic acid 
• 187083-86-9 (S)-1-benzyloxy-4-(3,5-dimethoxyphenyl)-2-methylbutane 
• 116435-46-2 5-(3,5-Dimethoxy-phenyl)-imidazolidine-2,4-dione 
• 216700-51-5 (E)-1-(2-hydroxy-4,6-diisopropoxyphenyl)-3-(3,5-dimethoxyphenyl)propenone 

Relevant articles and documents

A new porous Co(ii)-metal-organic framework for high sorption selectivity and affinity to CO2and efficient catalytic oxidation of benzyl alcohols to benzaldehydes

Herein, we report a new 3D porous Co(ii)-based metal-organic framework catalyst (Me2NH2)2[Co3(L)2(H2O)2]·2DMF (MOF I), which has been successfully prepared by using Co(ii) ions and rigid V-shaped 3,5-di(2,4-dicarboxylphenyl)pyridine (H4L) via the solvothermal reaction. Structural analysis reveals that I displays a porous structure with the pore size of 16.2 × 7.2 ?2 based on the trinuclear [Co3(COO)4(H2O)2N2] secondary building units (SBUs). Gas sorption experiments on the guest free sample I′ reveals a high capacity and selectivity to CO2 over CH4. And further, the catalytic explorations of the I′-catalyzed system (I′: 3 mol%; proline: 40 mol%; CH3CN: 2 mL) reveal that benzyl alcohols with different structures can be efficiently transformed into benzyl alcohols without by-products under mild conditions.

4CzIPN catalyzed photochemical oxidation of benzylic alcohols

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Radical induced disproportionation of alcohols assisted by iodide under acidic conditions

The disproportionation of alcohols without an additional reductant and oxidant to simultaneously form alkanes and aldehydes/ketones represents an atom-economical transformation. However, only limited methodologies have been reported, and they suffer from a narrow substrate scope or harsh reaction conditions. Herein, we report that alcohol disproportionation can proceed with high efficiency catalyzed by iodide under acidic conditions. This method exhibits high functional group tolerance including aryl alcohol derivatives with both electron-withdrawing and electron-donating groups, furan ring alcohol derivatives, allyl alcohol derivatives, and dihydric alcohols. Under the optimized reaction conditions, a 49% yield of 5-methyl furfural and a 49% yield of 2,5-diformylfuran were obtained simultaneously from 5-hydroxymethylfurfural. An initial mechanistic study suggested that the hydrogen transfer during this redox disproportionation occurred through the inter-transformation of HI and I2. Radical intermediates were involved during this reaction.