6044-68-4

Basic information

• Product Name: Acrolein dimethyl acetal
• Synonyms: Acroleindimethylacetal,99%;ACROLEIN DIMETHYL;1,1-Dimethoxyprop-2-ene;2-Propenal, dimethyl acetal;3,3-Dimethoxyprop-1-ene;Acrylaldehyde dimethyl acetal;Propenal dimethyl acetal;Acrolein DiMethyl Acetal , 97.0%(GC)
• CAS NO: 6044-68-4
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 227-936-4
• Product Categories: Pharmaceutical Intermediates
• Mol File: 6044-68-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 89-90 °C(lit.)
• Flash Point: 27 °F
• Appearance: colorless clear liquid
• Density: 0.862 g/mL at 25 °C(lit.)
• Vapor Pressure: 65.961mmHg at 25°C
• Refractive Index: n20/D 1.395(lit.)
• Storage Temp.: 2-8°C
• BRN: 1700037
• CAS DataBase Reference: Acrolein dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: Acrolein dimethyl acetal(6044-68-4)
• EPA Substance Registry System: Acrolein dimethyl acetal(6044-68-4)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25-29-33
• RIDADR: UN 3384 6.1/PG 1
• WGK Germany: 3
• RTECS: UC8500000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 6044-68-4(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Purification Methods

Fractionally distil it (after adding 0.5g of hydroquinone) under reduced pressure through an all glass column (40cm x 2.5 cm) packed with glass helices and provided with a heated jacket and a total reflux variable take-off head. Stainless steel Lessing rings (1/8 x 1/8 in) or gauze have also been used as packing. It is a highly flammable and TOXIC liquid; keep away from the skin. [Hall & Stern J Chem Soc 2657 1955, Beilstein 1 IV 3437.]

InChI:InChI=1/C5H10O2/c1-4-5(6-2)7-3/h4-5H,1H2,2-3H3

Synthetic route

methanol (67-56-1) + acrolein (107-02-8) → 3,3-dimethoxyprop-1-ene (6044-68-4) + acrylic acid methyl ester (292638-85-8)

Conditions	Yield
With oxygen; Pd5-Bi2-Fe1/(100)SiO2-MgO for 4h;	A n/a B 91.5%

methanol (67-56-1) + allyl n-butyl ether (3739-64-8) → 3,3-dimethoxyprop-1-ene (6044-68-4) + 3-n-butyloxy-3-methoxy-1-propene (106521-18-0)

Conditions	Yield
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation;	A 25% B 37%

methanol (67-56-1) + Allyl ether (557-40-4) → 3,3-dimethoxyprop-1-ene (6044-68-4) + 3-allyloxy-3-methoxy-1-propene (113443-66-6)

Conditions	Yield
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation;	A 9% B 35%
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation;	A 9% B 35%

3-chloropropionaldehyde dimethyl acetal (35502-06-8) → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
With potassium hydroxide

3-bromopropanal dimethyl acetal (36255-44-4) + sodium methylate (124-41-4) → 3,3-dimethoxyprop-1-ene (6044-68-4)

1,1,3-trimethoxypropane (14315-97-0) → 3,3-dimethoxyprop-1-ene (6044-68-4) + dimethoxypropene (78300-84-2)

Conditions	Yield
With quinoline; diisopropyl sulfate at 350℃;
With quinoline; diisopropyl sulfate at 350℃; entsteht ein Gemisch der stereoisomeren;

3-bromopropanal dimethyl acetal (36255-44-4) + sodium acetate (127-09-3) + acetic acid (64-19-7) → 3,3-dimethoxyprop-1-ene (6044-68-4)

methanol (67-56-1) + acrolein (107-02-8) → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
With toluene-4-sulfonic acid; Petroleum ether
With copper dichloride

methanol (67-56-1) + Methoxyallene (13169-00-1) → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
With toluene-4-sulfonic acid In diethyl ether Heating;

acrolein (107-02-8) + trimethyl orthoformate (149-73-5) → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
With ammonium nitrate In methanol
With ammonium nitrate In methanol for 5h; Ambient temperature;
With ammonium nitrite In methanol for 8h; Heating;

hydrogenchloride (7647-01-0) + methanol (67-56-1) + acrolein (107-02-8) → 3,3-dimethoxyprop-1-ene (6044-68-4) + 3-methoxy-1-propanal (2806-84-0)

Conditions	Yield
at 25 - 40℃; Kinetics;

3-chloropropionaldehyde dimethyl acetal (35502-06-8) + potassium hydroxide → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
beim Destillieren;

quinoline (91-22-5) + diisopropyl sulfate (2973-10-6) + 1,1,3-trimethoxypropane (14315-97-0) → methanol (67-56-1) + 3,3-dimethoxyprop-1-ene (6044-68-4) + acrolein (107-02-8) + 1,3-dimethoxy-propene

Conditions	Yield
at 350℃; Pyrolyse des Dampfes.Pyrolysis;

1,1,3-trimethoxypropane (14315-97-0) + aluminium oxide → methanol (67-56-1) + 3,3-dimethoxyprop-1-ene (6044-68-4) + acrolein (107-02-8) + 1,3-dimethoxy-propene

Conditions	Yield
at 228℃; Pyrolyse des Dampfes.Pyrolysis;

acrolein (107-02-8) → 3,3-dimethoxyprop-1-ene (6044-68-4)

Conditions	Yield
With hydroquinone In methanol

3,3-dimethoxyprop-1-ene (6044-68-4) + 1-[(4-chlorophenyl)methylene]-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide (80414-54-6) → 7-chloro-10-methoxy-3,3-dimethyl-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	98%

3,3-dimethoxyprop-1-ene (6044-68-4) + C36H42N2O7S → C39H48N2O9S

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In dichloromethane at 20℃; for 5h; Cross Metathesis; Inert atmosphere; chemoselective reaction;	97%
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 5h; Inert atmosphere;	97%
With Hoveyda-Grubbs catalyst second generation In dichloromethane at 20℃; for 5h; Inert atmosphere;

3,3-dimethoxyprop-1-ene (6044-68-4) + C12H13ClN2O → 6-chloro-10-methoxy-3,3-dimethyl-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	96%

3,3-dimethoxyprop-1-ene (6044-68-4) + bis-(phenylthio)-dibutylstannane (14365-16-3) → (E,Z)-1-methoxy-3-phenylthio-1-propene (150748-90-6)

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at -78℃; for 0.5h;	93%

3,3-dimethoxyprop-1-ene (6044-68-4) + 1-benzylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide (42953-83-3) → 10-methoxy-3,3-dimethyl-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Catalytic behavior; Mechanism; Kinetics; Solvent; Reagent/catalyst; Sealed tube; regioselective reaction;	93%

3,3-dimethoxyprop-1-ene (6044-68-4) + C14H17N3O2 → N-(10-methoxy-3,3-dimethyl-1-oxo-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-7-yl)acetamide

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	93%

3,3-dimethoxyprop-1-ene (6044-68-4) + 1-benzylidene-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide (42953-83-3) → C16H20N2O2

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Catalytic behavior; Reagent/catalyst;	93%

3,3-dimethoxyprop-1-ene (6044-68-4) + benzyl chloroformate (501-53-1) → ((E)-3-methyloxy-allyl)-carbamic acid benzyl ester (1075689-61-0)

Conditions	Yield
Stage #1: 3,3-dimethoxyprop-1-ene In benzene-d6 at 23℃; Stage #2: benzyl chloroformate With potassium carbonate In tetrahydrofuran; benzene-d6 at 23℃; for 12h; Further stages.;	92%

3,3-dimethoxyprop-1-ene (6044-68-4) + C13H14N2O3 → 10-methoxy-6,6-dimethyl-4b,6,7,10,10a,11-hexahydro-8H-[1,3]dioxolo[4',5':5,6]indeno[1,2-c]pyrazolo[1,2-a]pyrazol-8-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	92%

3,3-dimethoxyprop-1-ene (6044-68-4) + (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol (104863-92-5) → (2S,4S,5R)-4-Methyl-5-phenyl-2-vinyl-oxazolidine-3-carboxylic acid benzyl ester (113323-06-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 5h; Heating;	91%

3,3-dimethoxyprop-1-ene (6044-68-4) + phosphorous acid trimethyl ester (121-45-9) → dimethyl (1-methoxyprop-2-enyl)phosphonate (80986-52-3)

Conditions	Yield
Stage #1: 3,3-dimethoxyprop-1-ene With phosphorus trichloride for 0.25h; Inert atmosphere; Cooling; Stage #2: phosphorous acid trimethyl ester at 20℃; for 1h; Inert atmosphere; Cooling;	91%
With phosphorus trichloride In toluene for 3h; Ambient temperature;	82%

3,3-dimethoxyprop-1-ene (6044-68-4) + (1Z)-5,5-dimethyl-1-[(4-nitrophenyl)methylidene]-3-oxopyrazolidin-1-ium-2-ide (77396-68-0) → 10-methoxy-3,3-dimethyl-7-nitro-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	91%

3,3-dimethoxyprop-1-ene (6044-68-4) + (1S,2R)-(+)-2-chloro-N-(2-hydroxy-1-methyl-2-phenylethyl)acetamide (16251-50-6) → 2-Chloro-1-((2S,4S,5R)-4-methyl-5-phenyl-2-vinyl-oxazolidin-3-yl)-ethanone (137314-81-9)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 10h; Heating;	90%

3,3-dimethoxyprop-1-ene (6044-68-4) → methylallylether (627-40-7)

Conditions	Yield
With benzo[1,3,2]dioxaborole In benzene Ambient temperature;	88%

3,3-dimethoxyprop-1-ene (6044-68-4) + 1-[(4-bromophenyl)methylene]-5,5-dimethyl-3-oxopyrazolidin-1-ium-2-ide (88740-94-7) → 7-bromo-10-methoxy-3,3-dimethyl-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	88%

3,3-dimethoxyprop-1-ene (6044-68-4) + (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol (5627-22-5, 6138-10-9, 6708-49-2, 20181-49-1, 29084-16-0, 54933-92-5, 63598-21-0, 95839-12-6, 95839-13-7) → (R)-4,6-O-prop-2-enylidene-β-D-glucopyranosylbenzene (946411-12-7)

Conditions	Yield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 25℃; for 24h;	87%

3,3-dimethoxyprop-1-ene (6044-68-4) + ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (130539-43-4) → ethyl 4,6-O-allylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 1.5h;	86%

3,3-dimethoxyprop-1-ene (6044-68-4) + C14H16N2O3 → methyl 10-methoxy-3,3-dimethyl-1-oxo-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazole-7-carboxylate

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	86%

C31H40O11 (943239-55-2) + 3,3-dimethoxyprop-1-ene (6044-68-4) → C34H42O11 (943239-56-3)

Conditions	Yield
With (1S)-10-camphorsulfonic acid In dichloromethane at 20℃; for 3.5h; Temperature; Reagent/catalyst;	85.1%

3,3-dimethoxyprop-1-ene (6044-68-4) + norephedrine ortho-bromobenzamide → (2-Bromo-phenyl)-((2S,4S,5R)-4-methyl-5-phenyl-2-vinyl-oxazolidin-3-yl)-methanone

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 10h; Heating;	85%

3,3-dimethoxyprop-1-ene (6044-68-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(3,3-dimethoxypropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (259526-19-7)

Conditions	Yield
With Wilkinson's catalyst In dichloromethane for 24h;	85%
tris(triphenylphosphine)rhodium(I) chloride In dichloromethane stirred for 1 d; fractionated; elem. anal.;	85%
With Wilkinson's catalyst In dichloromethane at 20℃; Addition; hydroboration;	75%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; bis-diphenylphosphinomethane In dichloromethane at 20℃; for 18h; Inert atmosphere; Sealed tube;	29%

morpholine (110-91-8) + 2-bromobutene (23074-36-4) + 3,3-dimethoxyprop-1-ene (6044-68-4) → 4-((E)-2-Ethyl-5,5-dimethoxy-pent-2-enyl)-morpholine (76251-71-3)

Conditions	Yield
palladium diacetate at 125℃; for 48h;	84%

3,3-dimethoxyprop-1-ene (6044-68-4) + (-)-N-cyanomethylphenylglycinol (111980-33-7) → (-)-(2R,4R)-2-(methoxyethyl)-N-cyanomethyl-4-phenyl-1,3-oxazolidine (132609-60-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Heating;	83%

3,3-dimethoxyprop-1-ene (6044-68-4) + 1,5-anhydro-D-glucitol (154-58-5) → 1,5-anhydro-(R)-4,6-O-prop-2-enylidene-D-glucitol (946411-14-9)

Conditions	Yield
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 25℃; for 24h;	83%

3,3-dimethoxyprop-1-ene (6044-68-4) + norefedrine α-chloropropionamide (137314-75-1, 137431-00-6, 143060-09-7) → 2-Chloro-1-((2S,4S,5R)-4-methyl-5-phenyl-2-vinyl-oxazolidin-3-yl)-propan-1-one (137314-76-2, 137314-82-0, 142955-00-8) + 2-Chloro-1-((2R,4S,5R)-4-methyl-5-phenyl-2-vinyl-oxazolidin-3-yl)-propan-1-one (137314-76-2, 137314-82-0, 142955-00-8)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene for 14h; Heating;	A 82.8% B 7.2%
With pyridinium p-toluenesulfonate In benzene Heating; 4 Angstroem mol. sieves; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3,3-dimethoxyprop-1-ene (6044-68-4) + 1-nitrohexane (646-14-0) → 5-Dimethoxymethyl-3-pentyl-4,5-dihydro-isoxazole (88911-41-5)

Conditions	Yield
	82%

3,3-dimethoxyprop-1-ene (6044-68-4) + N-allyl-N-hydroxybenzamide (154491-53-9) → N-allyl-N-(1-methoxy-allyloxy)-benzamide (639512-99-5)

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene at 80℃;	82%

(Z)-5,5-dimethyl-1-(4-methylphenylmethylidene)-3-oxopyrazolidin-1-ium-2-ide (924663-44-5) + 3,3-dimethoxyprop-1-ene (6044-68-4) → 10-methoxy-3,3,7-trimethyl-2,3,4a,9,9a,10-hexahydro-1H-indeno[1,2-c]pyrazolo[1,2-a]pyrazol-1-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; lithium acetate at 40℃; for 12h; Sealed tube; regioselective reaction;	82%

3,3-dimethoxyprop-1-ene (6044-68-4) + 3-Phenylpropenol (104-54-1) → 4-phenyl-1,5-hexadien-3-ol

Conditions	Yield
Stage #1: 3-Phenylpropenol With C20H17ClPdSe2; water; toluene-4-sulfonic acid; bis(pinacol)diborane In methanol; dimethyl sulfoxide at 50℃; for 16h; Stage #2: 3,3-dimethoxyprop-1-ene In methanol; dimethyl sulfoxide at 50℃; for 20h;	81%

Upstream product

• 36255-44-4 3-bromopropanal dimethyl acetal 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 107-02-8 acrolein 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 3739-64-8 allyl n-butyl ether 
• 7647-01-0 hydrogenchloride 
• 14315-97-0 1,1,3-trimethoxypropane 
• 91-22-5 quinoline 
• 2973-10-6 diisopropyl sulfate 
• 35502-06-8 3-chloropropionaldehyde dimethyl acetal 
• 13169-00-1 Methoxyallene 
• 124-41-4 sodium methylate 

Downstream Products

• 25760-57-0 (3,3-dimethoxypropyl)trimethoxysilane 
• 14093-58-4 3-methoxy-1-heptene 
• 75066-94-3 (E)-1,1-dimethoxy-5-piperidino-3-hexene 
• 72908-61-3 trans,trans-sorbyl aldehyde dimethyl acetal 
• 73090-35-4 (2,2-Dimethoxy-1-methoxymethyl-ethylselanyl)-benzene 
• 156917-58-7 methyl 3-O-benzyl-4,6-O-prop-2-enylidene-β-D-glucopyranoside 
• 78177-40-9 3-methoxy-3-diphenylphosphinoylprop-1-ene 
• 174420-10-1 (2S,3R,4S)-4-Methoxy-2-methyl-1-trityloxy-hex-5-en-3-ol 
• 222611-17-8 4-allyl-4-methyl-2-vinyl-[1,3]dioxolane 
• 401913-32-4 (3S,4R,5R,6R,7S)-7-((2R,4R,5R,6R)-6-Isopropyl-2-methoxy-5-methyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl)-3-methoxy-5-methyl-6-triethylsilanyloxy-oct-1-en-4-ol 
• 443283-18-9 3-methoxy-6-[(4-methoxybenzyl)oxy]-5,7-dimethyl-1-octen-4-ol 
• 443283-16-7 [3S,4R,5R,6R,7R,8R]-6-[(tert-butyldimethylsilyl)oxy]-8-[(3,4-dimethoxybenzyl)oxy]-5,7-dimethyl-3-methoxynon-1-en-4-ol 

Relevant articles and documents

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