6380-23-0

Basic information

• Product Name: 3,4-DIMETHOXYSTYRENE
• Synonyms: 1,2-Dimethoxy-4-vinylbenzene;4-ethenyl-1,2-dimethoxybenzene;4-vinyl-1,2-dimethoxybenzene;3,4-DIMETHOXY-1-VINYLBENZENE;3,4-DIMETHOXYSTYRENE;4-vinylveratrole;3,4-DIMETHOXYSTYRENE, TECH.;Benzene, 4-ethenyl-1,2-dimethoxy-
• CAS NO: 6380-23-0
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 228-962-9
• Product Categories: Monomers;Polymer Science;Styrene and Functionalized Styrene Monomers;Aromatics;Miscellaneous Reagents
• Mol File: 6380-23-0.mol
• Article Data: 73

Chemical Properties

• Boiling Point: 120-125 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.109 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.021mmHg at 25°C
• Refractive Index: n20/D 1.571(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3,4-DIMETHOXYSTYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYSTYRENE(6380-23-0)
• EPA Substance Registry System: 3,4-DIMETHOXYSTYRENE(6380-23-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36-68-43-40
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 6380-23-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Occurrence

Reported found in coffee, rum and buckwheat.

Uses

3,4-Dimethoxy Styrene (~1% Hydroquinone as stabilizer) (cas# 6380-23-0) is a compound useful in organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 3451, 1980 DOI: 10.1016/S0040-4039(00)78712-0

InChI:InChI=1/C10H12O2/c1-4-8-5-6-9(11-2)10(7-8)12-3/h4-7H,1H2,2-3H3

Synthetic route

1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole (61078-14-6) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -55 - 20℃; Reagent/catalyst; Temperature; Time; Inert atmosphere;	97%
With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at -55 - 20℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere;	97%

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + trimethylsulphonium iodide (2181-42-2) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With n-butyllithium; lithium iodide In tetrahydrofuran; hexane from 0 degC to room temp.;	95%

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + methylenetriphenylarsorane (47025-43-4, 19365-61-8) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane for 1h; Ambient temperature;	95%

malonic acid (141-82-2) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0) + 3,4-dimethoxy-trans-cinnamic acid (14737-89-4)

Conditions	Yield
With pyridine; acetic acid at 130℃; for 0.133333h; Knoevenagel-Doebner reaction; microwave irradiation;	A 4 % Spectr. B 91%

dimethylsulfone (67-71-0) + (3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With platinum on carbon; potassium tert-butylate; hydrogen In toluene under 1875.19 Torr; for 15h; Inert atmosphere; Reflux;	91%
With C15H25Cl2N3NiO3; potassium tert-butylate In toluene at 110℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere;	76%

Methyltriphenylphosphonium bromide (1779-49-3) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 4h; Inert atmosphere;	90%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane; cyclohexane at 0℃; for 4h; Inert atmosphere; Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran; hexane; cyclohexane at 20℃; for 10h; Wittig Olefination; Inert atmosphere;	89%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Schlenk technique; Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃;	89%

ethene (74-85-1) + 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation; di-μ-bromobis-(tritert-butylphosphine)dipalladium(I) In tetrahydrofuran at 60℃; under 7500.75 Torr; for 16h; Autoclave;	90%

(trimethylsilyl)methylmagnesium chloride (13170-43-9) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
Stage #1: (trimethylsilyl)methylmagnesium chloride; 3,4-dimethoxy-benzaldehyde In tetrahydrofuran at 0 - 20℃; Peterson Olefination; Inert atmosphere; Stage #2: With bis(trifluoromethanesulfonyl)amide In 1,2-dichloro-ethane at 20℃; for 0.25h; Peterson Olefination;	89%

methyl-triphenylphosphonium iodide (2065-66-9) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran at 20℃; for 24h;	87%
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran for 1h; Inert atmosphere; Stage #2: 3,4-dimethoxy-benzaldehyde In tetrahydrofuran at 25℃; for 24h; Wittig reaction; Inert atmosphere;	75.2%
With tert-butoxide In tetrahydrofuran at 0℃; Wittig reaction;	60%

Methyl phenyl sulfone (3112-85-4) + (3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With sodium hydride In mineral oil at 135℃; for 7h; Inert atmosphere; Schlenk technique;	85%

Triethoxyvinylsilane (78-08-0) + 1-iodo-3,4-dimethoxybenzene (5460-32-2) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With sodium hydroxide In methanol; water at 100℃; for 8h; Hiyama Coupling; Sealed tube;	78%

carbon dioxide (124-38-9) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + carbonic acid dimethyl ester (616-38-6) → [2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-carbamic acid methyl ester + 3,4-dimethoxystyrene (6380-23-0) + N,N-dimethyl-3,4-dimethoxy-β-phenethylamine (3490-05-9) + [2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid methyl ester (35690-71-2)

Conditions	Yield
at 130℃; under 90007.2 - 97507.8 Torr; for 24h;	A n/a B n/a C n/a D 77%

1-(3,4-dimethoxyphenyl)ethanol (5653-65-6) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With 1-hexyl-3-methyl-1-imidazolium bromide at 140℃; for 0.2h; Microwave irradiation; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;	74%
With toluene-4-sulfonic acid In chloroform for 8h;	58%
Multi-step reaction with 2 steps 1: diethyl ether; CaCl2; hydrogen chloride / 0 °C 2: pyridine View Scheme
at 120℃; for 0.25h; Microwave irradiation; Ionic liquid;

dimethylsulfone (67-71-0) + (3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxystyrene (6380-23-0) + hydrogen (1333-74-0)

Conditions	Yield
With 1,10-Phenanthroline; potassium tert-butylate; iron(II) chloride In toluene at 120℃; for 24h; Julia Olefin Synthesis; Inert atmosphere; Schlenk technique;	A 74% B n/a

3,4-dimethoxy-benzaldehyde (120-14-9) + Methylenetriphenylphosphorane (19493-09-5) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
In 1,4-dioxane; water Inert atmosphere;	73%
Wittig reaction;
at 20℃; for 10h; Wittig Olefination;

dimethylsulfone (67-71-0) + (3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxystyrene (6380-23-0) + 4-isopropenyl-1,2-dimethoxybenzene (30405-75-5)

Conditions	Yield
With C15H25Br2N3NiO3; potassium tert-butylate In toluene at 110℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	A 72% B 6%
With C24H20ClN2OPRu; potassium tert-butylate In 1,4-dioxane at 125℃; for 5h; Inert atmosphere; Schlenk technique; Glovebox;	A 69% B 10 %Spectr.

4-Bromoveratrole (2859-78-1) + C8H16AlNO → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 60℃; for 12h;	59%

[2-(3,4-dimethoxyphenyl)-ethyl](ethyl)amine (39792-99-9) + epichlorohydrin (106-89-8) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
In chlorobenzene at 115℃;	56%

3,4-dimethoxyphenethyl bromide (40173-90-8) + ephedrine (299-42-3) → 3,4-dimethoxystyrene (6380-23-0) + (-)-(1R,2S)-N-(3,4-dimethoxyphenethyl)ephedrine (130459-47-1)

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Heating;	A 54% B 34%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + epichlorohydrin (106-89-8) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
In chlorobenzene at 115℃;	47%

3,4-dimethoxyphenethyl bromide (40173-90-8) + 1-(1-phenylethyl)-1,2,3,4-tetrahydroquinoline-2-carbonitrile → 3,4-dimethoxystyrene (6380-23-0) + 2-[2-(3,4-dimethoxyphenyl)ethyl]-1-(1-phenylethyl)-1,2,3,4-tetrahydroquinoline-2-carbonitrile (1087319-37-6)

Conditions	Yield
Stage #1: 1-(1-phenylethyl)-1,2,3,4-tetrahydroquinoline-2-carbonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -20℃; Inert atmosphere; Stage #2: 3,4-dimethoxyphenethyl bromide In tetrahydrofuran; Hexachlorobutadiene at -60 - 20℃; for 12h;	A n/a B 35%

3,4-dimethoxyphenethyl bromide (40173-90-8) + (1R,2R)-pseudoephedrine (321-97-1) → 3,4-dimethoxystyrene (6380-23-0) + (-)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine (130459-44-8)

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In ethanol for 60h; Heating;	A n/a B 29%

pyrrole (109-97-7) + 3,4-dimethoxyphenethyl bromide (40173-90-8) → C14H17NO2 + 3,4-dimethoxystyrene (6380-23-0) + 1-[2-(3,4-dimethoxyphenyl)ethyl]-1H-pyrrole (56014-51-8)

Conditions	Yield
Stage #1: pyrrole With potassium hydroxide; 18-crown-6 ether In benzene for 2h; Heating; Stage #2: 3,4-dimethoxyphenethyl bromide In benzene Heating; Further stages.;	A 23% B 27% C 27%

pyrrole (109-97-7) + 1-(3,4-dimethoxyphenyl)-2-(p-toluenesulfonyloxy)ethane (75010-39-8) → C14H17NO2 + 3,4-dimethoxystyrene (6380-23-0) + 1-[2-(3,4-dimethoxyphenyl)ethyl]-1H-pyrrole (56014-51-8)

Conditions	Yield
Stage #1: pyrrole With potassium hydroxide; 18-crown-6 ether In benzene for 2h; Heating; Stage #2: 1-(3,4-dimethoxyphenyl)-2-(p-toluenesulfonyloxy)ethane In benzene Heating; Further stages.;	A 4% B 4% C 9%

pyridine (110-86-1) + 4-(1-chloro-ethyl)-1,2-dimethoxy-benzene (50919-04-5) → 3,4-dimethoxystyrene (6380-23-0)

4-(1-chloro-ethyl)-1,2-dimethoxy-benzene (50919-04-5) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With pyridine

methyl magnesium iodide (917-64-6) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
und Destillation des Reaktionsprodukts;
With diethyl ether Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts unter vermindertem Druck auf Siedetemperatur;

3,4-dimethoxy-trans-cinnamic acid (14737-89-4) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With quinoline; copper(II) sulfate at 220℃;

N-<3,4-Dimethoxy-α-methyl-benzyl>-glycin-methyl-ester (1019628-47-7) → 3,4-dimethoxystyrene (6380-23-0)

Conditions	Yield
With sodium hydroxide In ethanol

imidazolidone (120-93-4) + 3,4-dimethoxyphenethyl bromide (40173-90-8) → 3,4-dimethoxystyrene (6380-23-0) + 1-<2-(3,4-dimethoxyphenyl)ethyl>imidazolidin-2-one (74996-66-0)

Conditions	Yield
With sodium hydride 1) benzene, reflux, 4 h 2) benzene, reflux, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

3,4-dimethoxystyrene (6380-23-0) → 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0)

Conditions	Yield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 4h; Wacker Oxidation;	100%
With perchloric acid; oxygen; palladium diacetate; p-benzoquinone; sodium nitrite In methanol; water at 20℃; for 24h; Wacker Oxidation; Schlenk technique; Sealed tube; Green chemistry;	95%
With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Wacker-Tsuji Olefin Oxidation; Inert atmosphere;	87%
With chromium(VI) oxide; palladium dichloride In water; acetonitrile at 20 - 60℃; for 24h; Wacker-Tsuji Olefin Oxidation;	75%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C22H24CuN4; dihydrogen peroxide In water at 40℃; for 7.5h; pH=2; Reagent/catalyst;

3,4-dimethoxystyrene (6380-23-0) → 4-ethylveratrole (5888-51-7)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium; isopropyl alcohol; nickel dichloride In tetrahydrofuran at 20 - 76℃; Inert atmosphere; chemoselective reaction;	99%
With hydrogen In methanol at 20℃; for 18h; chemoselective reaction;	99%
With hydrogen at 80℃; under 7500.75 Torr; for 1h; Autoclave;	94%
With hydrogen; platinum(IV) oxide In acetic acid	54.9%
With palladium 10% on activated carbon; hydrogen at 20℃; for 18h; Sealed tube;	83 mg

3,4-dimethoxystyrene (6380-23-0) + 4-chlorobenzonitrile (100-00-5) → 1,2-Dimethoxy-4-[2-(4-nitrophenyl)ethenyl]benzene (51042-54-7)

Conditions	Yield
With C32H27N4O2Pd(1+)*BF4(1-); sodium acetate at 140℃; for 12h; Inert atmosphere; Schlenk technique;	99%
With tetrabutylammomium bromide; palladium diacetate; silica gel; potassium carbonate for 0.75h; Neat (no solvent);	87%

3,4-dimethoxystyrene (6380-23-0) → (R)-2-hydroxy-1-(3,4-dimethoxyphenyl)ethanol (326491-79-6)

Conditions	Yield
With osmium(VIII) oxide; potassium carbonate; potassium hexacyanoferrate(III); 1,4-bis(9-O-dihydroquinidine)phthalazine In water; toluene; tert-butyl alcohol at 0℃; for 24h; Sharpless asymmetric dihydroxylation;	97%
With AD-mix β In water; tert-butyl alcohol at 0℃; Sharpless Dihydroxylation;

3,4-dimethoxystyrene (6380-23-0) + 3-bromo-2H-pyran-2-one (19978-32-6) → C15H15BrO4

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol at 80℃; for 120h; Diels-Alder cycloaddition;	97%

3,4-dimethoxystyrene (6380-23-0) → 2-(3,4-dimethoxyphenyl)oxirane (140687-75-8, 102104-61-0)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 0.666667h; Ambient temperature;	96%
With PS-DVB supported phthalic anhydride; urea-hydrogen peroxide In dichloromethane at 20℃;	77%

3,4-dimethoxystyrene (6380-23-0) + acrylic acid n-butyl ester (141-32-2) → n-butyl (E)-3-(3,4-dimethoxyphenyl)acrylate

Conditions	Yield
With Cl2Ru=CHPh(PCy3)[bis(1,3-Mes-2-ylimidazolidine)] In dichloromethane at 40℃; for 12h;	96%

3,4-dimethoxystyrene (6380-23-0) → C20H24O6 (1192036-78-4)

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃;	96%

3,4-dimethoxystyrene (6380-23-0) + phenyl formate (1864-94-4) → C17H18O4

Conditions	Yield
With formic acid; palladium diacetate; CyJohnPhos In toluene at 90℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	96%

3,4-dimethoxystyrene (6380-23-0) + 1-Iodonaphthalene (90-14-2) → (E)-1-(3,4-dimethoxystyryl)naphthalene (23833-70-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; N,N-dimethyl-formamide; lithium chloride at 110℃; for 6h; Heck Reaction; Inert atmosphere;	96%

3,4-dimethoxystyrene (6380-23-0) → β-hydroxy-3,4-dimethoxy phenethyl alcohol (13443-56-6)

Conditions	Yield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 12h; Sealed tube;	95%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 16h;	94%
With pyridine; osmium(VIII) oxide In diethyl ether at 20℃; for 20h; dihydroxylation;	80%
Upjohn Dihydroxylation; Inert atmosphere;

1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione (31617-39-7) + 3,4-dimethoxystyrene (6380-23-0) → istradefylline (155270-99-8)

Conditions	Yield
Stage #1: 1,3-diethyl-7-methyl-1H-purine-2,6(3H,7H)-dione With pyridine; palladium diacetate; copper(II) acetate monohydrate; copper(l) chloride In N,N-dimethyl acetamide at 20℃; for 0.0833333h; Heck reaction; Inert atmosphere; Stage #2: 3,4-dimethoxystyrene In N,N-dimethyl acetamide at 120℃; for 20h; Heck reaction; Inert atmosphere;	95%

1-bromo-4-methoxy-benzene (104-92-7) + 3,4-dimethoxystyrene (6380-23-0) → 4,3’,4’-trimethoxystilbene (263327-99-7)

Conditions	Yield
With C33H33N2(1+)*Cl(1-); palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide for 2h; Heck Reaction; Inert atmosphere; Sealed tube; Heating;	95%

3,4-dimethoxystyrene (6380-23-0) + 5-Methyloxazol-4-carbonsaeure-methylester (41172-57-0) → (E)-methyl 2-(3,4-dimethoxystyryl)-5-methyloxazole-4-carboxylate (1096163-95-9)

Conditions	Yield
With 1,10-Phenanthroline; palladium(II) trifluoroacetate; silver trifluoroacetate In toluene at 130℃; for 16h;	95%

potassium cyanide + 3,4-dimethoxystyrene (6380-23-0) → 2‐(3,4‐dimethoxyphenyl)propionitrile (51698-53-4)

Conditions	Yield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 60℃; Sealed tube; Stage #2: 3,4-dimethoxystyrene With bis(1,5-cyclooctadiene)nickel (0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 60℃; for 18h; Sealed tube;	95%

2,3,4,5-tetrahydropyridine N-oxide (34418-91-2) + 3,4-dimethoxystyrene (6380-23-0) → 2-(3,4-Dimethoxy-phenyl)-hexahydro-isoxazolo[2,3-a]pyridine (79235-48-6)

Conditions	Yield
In toluene Heating;	93%

3,4-dimethoxystyrene (6380-23-0) + 8-iodo-3′,4′,5,7-tetramethoxyflavone (52222-81-8) → C29H28O8

Conditions	Yield
With potassium chloride; tetrabutylammomium bromide; potassium carbonate; palladium dichloride In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Heck Reaction; Inert atmosphere; regioselective reaction;	93%

3,4-dimethoxystyrene (6380-23-0) + phenyl formate (1864-94-4) → C17H18O4

Conditions	Yield
With 1,1'-bis(dicyclohexylphosphinocyclopentadienyl)iron; palladium diacetate; acetic acid In toluene at 90℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	93%

3,4-dimethoxystyrene (6380-23-0) + 2-(2-phenylethynyl)-1,4-benzoquinone (89845-28-3) → 2-(3,4-dimethoxyphenyl)-7-(phenylethynyl)-2,3-dihydrobenzofuran-5-ol (1432504-67-0)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In acetonitrile at 0℃; Inert atmosphere; Schlenk technique;	92%

3,4-dimethoxystyrene (6380-23-0) → 2‐(3,4‐dimethoxyphenyl)propionitrile (51698-53-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); hydrogen cyanide; (3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-6-(2-(diphenylphosphino)-6-isopropylphenoxy)-2,2-dimethyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Optical yield = 88 %ee; enantioselective reaction;	92%

3,4-dimethoxystyrene (6380-23-0) + C12H10O6 → dimethyl 2-((2-(3,4-dimethoxyphenyl)-5-hydroxy-2,3-dihydrobenzofuran-7-yl)methylene)malonate

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 0.166667h; regioselective reaction;	92%

3,4-dimethoxystyrene (6380-23-0) + 5-iodo-N,N,8-trimethylnaphthalen-2-amine → (E)-5-(3,4-dimethoxystyryl)-N,N,8-trimethylnaphthalen-2-amine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine; N,N-dimethyl-formamide; lithium chloride at 110℃; for 5h; Heck Reaction; Inert atmosphere;	92%

3,4-dimethoxystyrene (6380-23-0) + 4-methoxyphenylboronic acid (5720-07-0) → (S)-1,2-dimethoxy-4-(1-(4-methoxyphenyl)ethyl)benzene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C33H30N2O2; lithium tert-butoxide In methanol at 50℃; for 3h; Inert atmosphere; Glovebox; Sealed tube; enantioselective reaction;	92%

3,4-dimethoxystyrene (6380-23-0) + p-toluenesulfonylhydroxylamine (1593-60-8) → 1-(3,4-dimethoxyphenyl)-2-tosylethanone oxime (1377813-97-2)

Conditions	Yield
With tetrabutylammonium periodite In dichloromethane at -20 - 40℃; for 3h; Inert atmosphere;	91%

Upstream product

• 110-86-1 pyridine 
• 50919-04-5 4-(1-chloro-ethyl)-1,2-dimethoxy-benzene 
• 917-64-6 methyl magnesium iodide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 1019628-47-7 N-<3,4-Dimethoxy-α-methyl-benzyl>-glycin-methyl-ester 
• 120-93-4 imidazolidone 
• 40173-90-8 3,4-dimethoxyphenethyl bromide 
• 299-42-3 ephedrine 
• 321-97-1 (1R,2R)-pseudoephedrine 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 2181-42-2 trimethylsulphonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 77425-85-5 (trimethylsilyl)(tributylstannyl)methane 

Downstream Products

• 69151-24-2 4-(1,2-dibromo-ethyl)-1,2-dimethoxy-benzene 
• 86980-84-9 2-(3,4-Dimethoxyphenyl)-2,3,3a,4,5,6-hexahydropyrrolo<1,2-b>isoxazole 
• 63216-09-1 6,7-dimethoxy-1,4-phenanthrenequinone 
• 71642-81-4 N-[2-(3,4-dimethoxyphenyl)ethyl]piperidine 
• 5888-51-7 4-ethylveratrole 
• 140687-75-8 2-(3,4-dimethoxyphenyl)oxirane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 109980-42-9 1-(3',4'-dimethoxyphenyl)-6,7-dimethoxynaphthalene 
• 6256-06-0 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

The first one-pot metathesis-hydroformylation procedure: a straight synthesis of 2-arylpropanals from renewable 1-propenylbenzenes

Hydroformylation is a consolidated synthetic tool in the chemical industry, both in commodity and in the fine chemicals industry. Olefin metathesis has been largely employed in the petrochemical sector, and, more recently, in the synthesis of specialty chemicals. Although these reactions may be involved in the same synthetic route for various industrial chemicals, to the best of our knowledge, they have never been combined in a one-pot procedure. As a proof of concept, we have demonstrated in the present work that the ruthenium-catalyzed ethenolysis of renewable 1-propenylbenzenes followed by the rhodium-catalyzed hydroformylation of functionalized styrenes formed in the first step could be done in one pot. The integration of these reactions was not straightforward once the catalyst of the first step interfered with the catalyst of the second step. Under optimized conditions, it was possible to synthesize 2-arylpropanals, a class of compounds valuable as synthetic intermediates to access non-steroidal anti-inflammatory drugs, in overall yields of 85-90%, at low catalyst loadings.