122-84-9

Basic information

• Product Name: 4-Methoxyphenylacetone
• Synonyms: FEMA 2674;4-ANISYL ACETONE;4-METHOXYBENZYL METHYL KETONE;4-METHOXYPHENYLACETONE;4-ACETONYLANISOLE;1-(P-METHOXYPHENYL)-2-PROPANONE;3-(4-METHOXYPHENYL)-2-PROPANONE;1-(4-METHOXYPHENYL)-2-PROPANONE
• CAS NO: 122-84-9
• Molecular Formula: C10H12O2
• Molecular Weight: 164.20108
• EINECS: 204-578-7
• Product Categories: Aromatic Ketones (substituted);API intermediates;Aromatics;Miscellaneous Reagents;ketone
• Mol File: 122-84-9.mol
• Article Data: 96

Chemical Properties

• Melting Point: <-15 °C
• Boiling Point: 145 °C25 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: Clear light yellow to yellow-green/Liquid
• Density: 1.067 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00789mmHg at 25°C
• Refractive Index: n20/D 1.525(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: 3.084g/L at 25℃
• BRN: 2044332
• CAS DataBase Reference: 4-Methoxyphenylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxyphenylacetone(122-84-9)
• EPA Substance Registry System: 4-Methoxyphenylacetone(122-84-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25
• WGK Germany: 2
• RTECS: UC2990000
• TSCA: Yes
• Hazardous Substances Data: 122-84-9(Hazardous Substances Data)

Usage

Description

l-(p-Methoxyphenyl)-2-propanone has an odor and taste similar to anise. May be obtained by boiling α- or β-anetholglycol with a 20% solution of sulfuric acid, or from l-(p-methoxyphenyl)- propan-l,2-ol by treatment with diluted sulfuric acid.

Chemical Properties

Different sources of media describe the Chemical Properties of 122-84-9 differently. You can refer to the following data:
1. 1-(p-Methoxyphenyl)-2-propanone has an odor and taste similar to anise.
2. Pale Yellow Liquid

Occurrence

Reported found in Chinese star anise and in Russian star anise; also reported found in sweet and common fen nel, chervil (Anthriscus cerefolium) and Illicium verum and cherry

Uses

A volatile compound released by flowering plants to attractant insects

Preparation

Obtained by boiling α- or β-anetholglycol with a 2% solution of sulfuric acid, or from 1-(p-methoxyphenyl)-propan-1,2-ol by treatment with diluted sulfuric acid.

Taste threshold values

Taste characteristics at 15 ppm: sweet spicy, with green anisic, minty nuances.

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 1748, 1996 DOI: 10.1021/jo9518314

General Description

Asymmetric amination of 4-methoxyphenylacetone was studied.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion andother routes. A skin irritant. A flammable liquid.

InChI:InChI=1/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3

Synthetic route

para-iodoanisole (696-62-8) + acetone (67-64-1) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; caesium carbonate at 90℃; for 16h; Inert atmosphere; sealed vial;	98%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; [Pd(π-cinnamyl)Cl]2; caesium carbonate at 25℃; for 48h; Sealed tube; Inert atmosphere; Glovebox;	76%

1-bromo-2-(4-methoxyphenyl)propan-2-ol (98815-48-6) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With diethylzinc In dichloromethane at 20℃; for 2h;	95%

1-isopropenyl-4-methoxybenzene (1712-69-2) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene In methanol at 20℃; for 0.333333h;	92%
With oxone; sodium iodide In water; acetonitrile at 20℃; for 15h; Green chemistry;	85%
Stage #1: 1-isopropenyl-4-methoxybenzene With 2-Iodo-5-methylbenzenesulfonic acid In tert-butyl methyl ether; water; isopropyl alcohol at 22℃; for 0.0833333h; Inert atmosphere; Stage #2: With Oxone In tert-butyl methyl ether; water; isopropyl alcohol at 22℃; for 4h; Inert atmosphere; Further stages;	68%
With iodine; mercury(II) oxide Man laesst auf das entstandene Jodhydrin AgNO3 oder HgO einwirken;

Estragole (140-67-0) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With iron(III) chloride; palladium(II) trifluoroacetate; sodium 2,2,2-trifluoroacetate In water; acetonitrile at 30℃; Temperature; Wacker-Tsuji Olefin Oxidation; Inert atmosphere; Darkness;	92%
Multi-step reaction with 2 steps 1: yellow HgO; absolute methanol; iodine 2: alcoholic potash / Durch Einw. von 20prozentiger Schwefelsaeure das Reaktionsprodukt View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: Rh((1,8-bis(imidazolin-2-ylidene)-3,6-di(tert-butyl)carbazolide)homoallyl) / benzene-d6 / 2 h / 20 °C / Inert atmosphere; Schlenk technique View Scheme

1-(2,2-dimethoxypropyl)-4-methoxybenzene → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With SO3H silica gel In methanol at 50℃; for 2h; Inert atmosphere;	92%

1-(2-Iodo-1-methoxy-1-methyl-ethyl)-4-methoxy-benzene (98236-12-5) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;	90%

1-(4-Methoxy-phenyl)-propan-2-one O-methyl-oxime (94169-18-3) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With hydrogenchloride In methanol at 65℃; for 10h;	90%

para-iodoanisole (696-62-8) + acetylacetone (123-54-6) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With copper(l) iodide; potassium phosphate tribasic trihydrate In dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;	89%

1-(4-methoxyphenyl)-2-methyl-3-phenylpropan-2-ol (65739-10-8) → 4-methoxybenzyl methyl ketone (122-84-9) + 1-phenyl-acetone (103-79-7)

Conditions	Yield
With 2,3,5-trimethyl-pyridine; [Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(5,5'-bis(trifluoromethyl)-2,2'-bipyridyl)](PF6); thiophenol In dichloromethane at 20℃; Sealed tube; Inert atmosphere; Irradiation;	A 5% B 89%

4-chloromethoxybenzene (623-12-1) + acetone (67-64-1) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With potassium phosphate; 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate at 90℃; for 18h; Inert atmosphere; Schlenk technique;	88%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 2-methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine; caesium carbonate at 90℃; for 24h; Kinetics; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube;	84%
With 2-methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine; palladium cinnamyl chloride; caesium carbonate at 90℃; for 12h; Schlenk technique; Inert atmosphere;	84%

1-methoxy-4-(2-nitro-1(Z)-propenyl)benzene (207511-16-8) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With formaldehyd In 1,4-dioxane; perchloric acid; dichloromethane for 0.333333h; Ambient temperature;	87%
With hydrogenchloride; iron In methanol; water for 0.5h; Heating;	80%
With aluminium; nickel dichloride In tetrahydrofuran Substitution;	79%

methyl magnesium iodide (917-64-6) + 2-chloro-1-(4-methoxyphenyl)ethanone (2196-99-8) → 1-(4-methoxyphenyl)-2-methylpropan-2-ol (35144-39-9) + 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
In tetrahydrofuran for 16h; Ambient temperature;	A 85% B 10%
In tetrahydrofuran at 20℃; for 16h;	A 85% B 10%

(E)-3-(4-methoxyphenyl)-2-methylacrylic acid (13048-81-2, 40527-52-4, 13048-80-1) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene at 25 - 110℃; for 2h;	85%
Multi-step reaction with 2 steps 1: thionyl chloride / tetrachloromethane / 0.5 h / 35 °C 2: sodium azide; tetrabutylammomium bromide; water / tetrachloromethane / 1.5 h / Reflux View Scheme

4-methoxyphenyl 1H-imidazole-1-sulfonate (1139705-25-1) + acetone (67-64-1) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; chemoselective reaction;	84%
With 4-fluorophenyl tosylate; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 10h; Inert atmosphere;	84%

2-nitro-1-(4-methoxylphenyl) propane (29865-49-4) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With hydrogenchloride; iron In methanol; water for 0.5h; Heating;	82%
With chloro-trimethyl-silane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid 1.) dichloromethane, 30 min, 0 degC; 2.) dichloromethane, 30 min, room temperature; Yield given. Multistep reaction;

4-(4'-methoxyphenyl)-2,5-dimethyl-1,3-dioxolane → 1-chloro-2-hydroxy-1-(4'-methoxyphenyl)propane (1227753-59-4) + 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0℃; for 0.5h; Mukaiyama reaction; Inert atmosphere;	A 16% B 80%
With titanium tetrachloride In dichloromethane at -30℃; for 0.5h; Mukaiyama reaction; Inert atmosphere;	A 66% B 30%

methanol (67-56-1) + 1-methoxy-4-(2-nitro-1(Z)-propenyl)benzene (207511-16-8) → 4-methoxybenzyl methyl ketone (122-84-9) + 1-methoxy-1-(4-methoxy-phenyl)-propan-2-one oxime

Conditions	Yield
With indium; chloro-trimethyl-silane at 25℃; for 5.5h; Reduction; Addition;	A n/a B 78%

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene (37629-51-9) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With trifluoroacetic acid; zinc In N,N-dimethyl-formamide for 0.25h;	75%

1-bromo-4-methoxy-benzene (104-92-7) + acetone (67-64-1) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With potassium phosphate; C37H56ClPPd at 50℃; for 21h; Sealed tube; Inert atmosphere;	70%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; [Pd(π-cinnamyl)Cl]2; caesium carbonate at 25℃; for 48h; Sealed tube; Inert atmosphere; Glovebox;	64%

trans-2-(p-methoxyphenyl)-3-methyloxirane + 2-fluoro-4,4,5,5-tetramethyl-1,3-dioxa-2-boracyclopentane → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	69%

1-bromo-4-methoxy-benzene (104-92-7) + sodium acetylacetonate (15435-71-9, 1118-67-8) → 4-methoxybenzyl methyl ketone (122-84-9) + 1-(4-methoxyphenyl)pentane-2,4-dione (210168-09-5)

Conditions	Yield
copper(l) iodide In N,N-dimethyl-formamide at 100 - 120℃; for 23h;	A 67% B 23%
copper(l) iodide In N,N-dimethyl-formamide at 100 - 120℃; for 23h;	A 67% B 26%

1-(4-methoxybenzyl)-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt (71017-75-9) + acetyl chloride (75-36-5) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With manganese; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl acetamide; acetonitrile at 20℃; for 6h; Inert atmosphere; Schlenk technique;	67%

4-(2-nitro-propenyl)-anisole (17354-63-1) → 4-methoxybenzyl methyl ketone (122-84-9) + 4-methoxyphenylacetone oxime (52271-41-7)

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid In methanol at 0 - 5℃; ceramic diaphragm, carbon-rod anode, platinum cathode, 4.5 F/mol, 0.1A, cathode potential -1.45 to -1.65V vs. SCE;	A 6% B 65%

para-iodoanisole (696-62-8) + chloroacetone (78-95-5) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate Ambient temperature; Al rod/nickel-sponge;	65%
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; i = 250 mA, nickel-sponge cathode;	65%

4-(4'-methoxyphenyl)-2,5-dimethyl-1,3-dioxolane → 1-chloro-2-hydroxy-1-(4'-methoxyphenyl)propane (1227753-59-4) + 4-methoxybenzyl methyl ketone (122-84-9) + 2-hydroxy-1-methoxy-1-(4'-methoxyphenyl)propane (21712-86-7)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 0.5h; Mukaiyama reaction; Inert atmosphere;	A 64% B 16% C 16%

2-(4-methoxyphenyl)-3-methyloxirane (51410-46-9) → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
With clay; potassium bromide In benzene for 0.25h; Ambient temperature;	61%

1-(1-phenylethyl)-2-methyleneaziridine + CH3OC6H4MgX → 4-methoxybenzyl methyl ketone (122-84-9)

Conditions	Yield
Stage #1: N-(1-Phenylethyl)-2-methyleneaziridine; CH3OC6H4MgX With copper(l) iodide; boron trifluoride diethyl etherate In tetrahydrofuran at -30 - 0℃; Ring cleavage; Stage #2: In tetrahydrofuran Hydrolysis; Further stages.;	60%

4-methoxybenzyl methyl ketone (122-84-9) → 2-methoxy-5-(2-oxopropyl)benzenesulfonyl chloride (80223-79-6)

Conditions	Yield
With chlorosulfonic acid at 0 - 20℃; for 2h;	100%
With chlorosulfonic acid	40%
With chlorosulfonic acid for 2h; Ambient temperature;	11.4 g

4-methoxybenzyl methyl ketone (122-84-9) + 2-Pentanone (107-87-9) → (R)‐2‐aminopentane (625-30-9, 33985-20-5, 54542-13-1, 63493-28-7) + (R)-(-)-p-methoxyamphetamine (58993-79-6)

Conditions	Yield
With Candida boidinii formate dehydrogenase; pyridoxal 5'-phosphate; Aspergillus terreus ω-trans aminase; Lysinibacillus fusiformis leucine dehydrogenase; ammonium formate; nicotinamide adenine dinucleotide In aq. buffer at 30℃; for 24h; pH=8.8; Catalytic behavior; Green chemistry; Enzymatic reaction;	A 99.7% B 99.4%

4-methoxybenzyl methyl ketone (122-84-9) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(1-(4-methoxyphenyl)propan-2-ylidene)-4-methylbenzenesulfonohydrazide (1379610-69-1)

Conditions	Yield
In methanol at 20℃; Inert atmosphere;	99.5%
In methanol at 70℃; Inert atmosphere;
In methanol Reflux;

4-methoxybenzyl methyl ketone (122-84-9) → 1-(4-methoxyphenyl)propan-2-ol (131029-01-1, 30314-64-8)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;	99%
With methanol; sodium tetrahydroborate at 0℃; for 2h; Inert atmosphere;	99%
With IrH2Cl[(iPr2PC2H4)2NH]; potassium tert-butylate; hydrogen In methanol at 20℃; under 7600.51 Torr; for 1h;	98%

4-methoxybenzyl methyl ketone (122-84-9) + benzylamine (100-46-9) → [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine (43229-65-8)

Conditions	Yield
With hydrogen; platinum on activated charcoal In ethanol	99%
With platinum on carbon; hydrogen In methanol at 20℃; under 2327.23 - 2844.39 Torr; Inert atmosphere;	99%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 0 - 20℃;	97%

trimethylsilyl cyanide (7677-24-9) + 4-methoxybenzyl methyl ketone (122-84-9) → 3-(4'-methoxyphenyl)-2-methyl-2-trimethylsilyloxypropanenitrile

Conditions	Yield
With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 5h;	99%
With cesium fluoride In acetonitrile at 20℃; for 0.8h;	97%
With montmorillonite K10 In acetone at 20℃; for 0.166667h; Catalytic behavior; Green chemistry;	96%

4-methoxybenzyl methyl ketone (122-84-9) → (R)-(-)-p-methoxyamphetamine (58993-79-6)

Conditions	Yield
With glucose dehydrogenase; D-Alanine; D-glucose; ω-transaminase ATA-117; pyridoxal 5'-phosphate; nicotinamide adenine dinucleotide; lactate dehydrogenase In dimethyl sulfoxide at 30℃; for 24h; pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;	99%
With pyridoxal 5'-phosphate; amine transaminase TA-P2-B01; isopropylamine In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	86%
With Cb-FDH formate dehydrogenase (variant) from Candida boidinii; Rs-PhAmDH amine dehydrogenase variant from the phenylalanine dehydrogenase from Rhodoccoccus species; NAD; ammonium formate In water at 30℃; for 24h; pH=8.5; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;	82%

4-methoxybenzyl methyl ketone (122-84-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 4-dimethylamino-3-(4-methoxyphenyl)-but-3-en-2-one

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 2h; Microwave irradiation;	99%

4-methoxybenzyl methyl ketone (122-84-9) + malononitrile (109-77-3) → 2-(1-(4-methoxyphenyl)propan-2-ylidene)malononitrile (69358-84-5)

Conditions	Yield
With ammonium acetate; acetic acid In benzene at 120℃; Knoevenagel Condensation; Dean-Stark;	98%
With ammonium acetate In acetic acid; benzene

4-methoxybenzyl methyl ketone (122-84-9) → (S)-(+)-1-(4-methoxyphenyl)propan-2-ol (131029-01-1)

Conditions	Yield
With Rhodococcus ruber alcohol dehydrogenase; NAD; isopropyl alcohol; magnesium chloride In aq. phosphate buffer at 30℃; pH=7; Catalytic behavior; Reagent/catalyst; Time; Inert atmosphere; Schlenk technique; Enzymatic reaction; enantioselective reaction;	98%
With D-glucose; Zygosaccharomyces rouxii cells In water at 28℃; for 1h;	82%
With bakers' yeast at 30℃; for 120h; Product distribution; further aryl ketones investigated;	80%

4-methoxybenzyl methyl ketone (122-84-9) → (S)-2-(4-methoxy-phenyl)-1-methyl-ethylamine (58993-78-5)

Conditions	Yield
With L-alanin; Bacillus subtilis L-alanine dehydrogenase; NAD-specific formate dehydrogenase; ω-transaminase ATA-113; pyridoxal 5'-phosphate; ammonium formate; nicotiamide adenine dinucleotide In dimethyl sulfoxide at 30℃; for 24h; pH=7; aq. phosphate buffer; optical yield given as %ee; enantioselective reaction;	98%
With pyridoxal 5'-phosphate; amine transaminase TA-P1-G05; isopropylamine In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	84%
Multi-step reaction with 2 steps 1: 79 percent / ammonium formate / Pd/C / methanol / 20 °C 2: Candida antarctica lipase B / 22 h / 28 °C View Scheme

4-methoxybenzyl methyl ketone (122-84-9) + methylmagnesium bromide (75-16-1) → 1-(4-methoxyphenyl)-2-methylpropan-2-ol (35144-39-9)

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone; methylmagnesium bromide In diethyl ether; benzene at 100℃; for 3h; Stage #2: With water; ammonium chloride In diethyl ether; benzene at 0℃;	98%
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;

4-methoxybenzyl methyl ketone (122-84-9) + 2-chloro-1,2-bis(4-methylphenyl)ethanone (71193-32-3) → 3-(4-methoxyphenyl)-1,2-di-p-tolylpentane-1,4-dione (1333377-93-7)

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #3: 2-chloro-1,2-bis(4-methylphenyl)ethanone With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 45℃; Inert atmosphere; optical yield given as %de;	98%

4-methoxybenzyl methyl ketone (122-84-9) → 4-methoxybenzonitrile (874-90-8)

Conditions	Yield
With aluminum (III) chloride; sodium nitrite In N,N-dimethyl-formamide at 90℃; for 4h; Schlenk technique;	98%
With oxygen; copper diacetate; ammonium carbonate; tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide at 120℃; for 5h; Schlenk technique;	59%

2-(2-bromophenyl)-1,3-dioxolan (34824-58-3) + 4-methoxybenzyl methyl ketone (122-84-9) → 1-(2-(1,3-dioxolan-2-yl)phenyl)-1-(4-methoxyphenyl)propan-2-one

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate at 70℃; for 18h; Inert atmosphere;	98%

4-methoxybenzyl methyl ketone (122-84-9) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-[(Z)-2-(4-methoxy-phenyl)-1-methyl-vinyloxy]-dimethyl-silane (82700-20-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran Ambient temperature;	97%

4-methoxybenzyl methyl ketone (122-84-9) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (R)-1-(4-methoxyphenyl)-N-((R)-1-phenylethyl)propan-2-amine (140173-30-4)

Conditions	Yield
With hydrogen; titanium(IV)isopropoxide In 1,2-dichloro-ethane at 20 - 45℃; under 7600.51 Torr; for 1.25h; Reagent/catalyst; Autoclave;	96%
(i) benzene, (ii) H2, Raney-Ni, EtOH; Multistep reaction;
With hydrogen; platinum(IV) oxide In methanol at 50℃; under 1500.15 Torr; for 12h;
With platinum on carbon; hydrogen In methanol at 60℃; for 24h;
Multi-step reaction with 2 steps 1: hydrogen; platinum on activated charcoal 2: L-Tartaric acid / ethanol View Scheme

trimethylsilyl cyanide (7677-24-9) + 4-methoxybenzyl methyl ketone (122-84-9) → C14H21NO2Si

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone With (R,R)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminoaluminum(III) chloride; (tert-Butoxycarbonylmethylene)triphenylphosphorane; Triphenylphosphine oxide In dichloromethane at -40℃; for 0.5h; Inert atmosphere; Stage #2: trimethylsilyl cyanide In dichloromethane at -40℃; for 10h; Inert atmosphere;	96%

4-methoxybenzyl methyl ketone (122-84-9) + 2,2-dihydroxy-1-phenyl-ethanone (1075-06-5) → 2-hydroxy-3-(4-methoxyphenyl)-1-phenylpentane-1,4-dione

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water at 20℃; for 24h; Reagent/catalyst; Aldol Condensation; Green chemistry; diastereoselective reaction;	95%

4-methoxybenzyl methyl ketone (122-84-9) + (R)-1-phenyl-ethyl-amine (3886-69-9) → C18H23NO*ClH

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone; (R)-1-phenyl-ethyl-amine With 2 % platinum on carbon; hydrogen In methanol for 3h; Stage #2: With hydrogenchloride In acetone for 2h; pH=2 - 3; Reagent/catalyst; Solvent;	95%

4-methoxybenzyl methyl ketone (122-84-9) + potassium cyanide (151-50-8) → 5-(4-methoxybenzyl)-5-methylimidazolidine-2,4-dione (13500-24-8)

Conditions	Yield
With ammonium carbonate In ethanol; water at 80℃; for 18h;	93%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 4-methoxybenzyl methyl ketone (122-84-9) → 6-fluoro-3-(4-methoxyphenyl)-2-methylquinoline-4-carboxylic acid (1609013-04-8)

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 48h; Pfitzinger Quinoline Synthesis;	93%
With potassium hydroxide In ethanol for 48h; Pfitzinger Quinoline Synthesis; Reflux;	93%

2-methyl-3-bromo-1-propene (1458-98-6) + 4-methoxybenzyl methyl ketone (122-84-9) → C14H18O2

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.5h; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide; mineral oil at -20 - 20℃; for 0.5h; Inert atmosphere;	93%

4-methoxybenzyl methyl ketone (122-84-9) + Benzhydrylamine (91-00-9) → N-diphenylmethyl-1-(4-methyloxyphenyl)propan-2-amine

Conditions	Yield
Stage #1: 4-methoxybenzyl methyl ketone; Benzhydrylamine With titanium(IV) isopropylate; trifluoroacetic acid In dichloromethane for 2h; Molecular sieve; Stage #2: With hydrogen under 38002.6 Torr; for 14h;	93%

4-methoxybenzyl methyl ketone (122-84-9) + methylmagnesium chloride (676-58-4) → 1-(4-methoxyphenyl)-2-methylpropan-2-ol (35144-39-9)

Conditions	Yield
In tetrahydrofuran; toluene at 8 - 12℃; for 1.75h;	93%

4-methoxybenzyl methyl ketone (122-84-9) + trimethylsulfoxonium iodide (1774-47-6) → 2-(4-methoxybenzyl)-2-methyloxirane

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 4-methoxybenzyl methyl ketone In dimethyl sulfoxide; mineral oil at 20℃; for 5h; Sealed tube; Inert atmosphere;	93%

Upstream product

• 51410-46-9 2-(4-methoxyphenyl)-3-methyloxirane 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 52271-41-7 4-methoxyphenylacetone oxime 
• 104-01-8 4-Methoxyphenylacetic acid 
• 108-24-7 acetic anhydride 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 63895-78-3 2-(4-methoxyphenyl)-3-oxobutanenitrile 
• 917-54-4 methyllithium 
• 79-24-3 Nitroethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 115348-15-7 N,N-diethyl-2-(4-methoxyphenyl)acetamide 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 5739-33-3 4-[3-(4-methoxy-phenyl)-thiopropionyl]-morpholine 
• 101287-18-7 1-(4-methoxy-phenyl)-2-methyl-3-[2]pyridyl-propan-2-ol 
• 126002-14-0 N-[2-(4-methoxyphenyl)-1-methyl-ethyl]formamide 
• 91350-54-8 5-(4-methoxyphenyl)-4-methylthiazol-2-amine 
• 26155-72-6 N'-[2-(4-Methoxy-phenyl)-1-methyl-eth-(E)-ylidene]-hydrazinecarbodithioic acid methyl ester 
• 20620-37-5 ethyl (2E)-2-cyano-4-(4-methoxyphenyl)-3-methylbut-2-enoate 
• 20620-37-5 α-Cyano-β-methyl-β-(p-methoxybenzyl)-acrylsaeure-ethylester 
• 91121-48-1 4-(4-methoxyphenyl)-3-methyl-3-butenoic acid 
• 91121-47-0 4-(4-methoxyphenyl)-3-methyl-2-butenoic acid 
• 137363-50-9 Thiocarbonic acid S-[1-(4-methoxy-phenyl)-2-oxo-propyl] ester O-methyl ester 
• 140870-27-5 Phenyl-acetic acid N'-[(E)-2-(4-methoxy-phenyl)-1-methyl-vinyl]-N,N'-dimethyl-hydrazide 
• 84571-60-8 6-Chloro-2-(4-methoxy-benzyl)-2-methyl-4-phenyl-1,2,3,4-tetrahydro-quinazoline 
• 81861-31-6 [2-(4-Methoxy-phenyl)-1-methyl-ethyl]-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine; hydrochloride 
• 35144-39-9 1-(4-methoxyphenyl)-2-methylpropan-2-ol 

Relevant articles and documents

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Markovnikov Wacker-Tsuji Oxidation of Allyl(hetero)arenes and Application in a One-Pot Photo-Metal-Biocatalytic Approach to Enantioenriched Amines and Alcohols

The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl compounds were synthesized with high conversions (>80%) and excellent selectivities (>90%). The key process was the transient formation of Pd nanoparticles that can activate oxygen, thus recycling the Pd(II) species necessary in the Wacker oxidative reaction. While light irradiation was strictly mandatory, the addition of the photocatalyst improved the reaction selectivity, due to the formation of the starting allyl(hetero)arene from some of the obtained by-products, thus entering back in the Wacker-Tsuji catalytic cycle. Once optimized, the oxidation reaction was combined in a one-pot two-step sequential protocol with an enzymatic transformation. Depending on the biocatalyst employed, i. e. an amine transaminase or an alcohol dehydrogenase, the corresponding (R)- and (S)-1-arylpropan-2-amines or 1-arylpropan-2-ols, respectively, could be synthesized in most cases with high yields (>70%) and in enantiopure form. Finally, an application of this photo-metal-biocatalytic strategy has been demonstrated in order to get access in a straightforward manner to selegiline, an anti-Parkinson drug. (Figure presented.).

Photoredox-Catalyzed Dehydrogenative Csp3-Csp2Cross-Coupling of Alkylarenes to Aldehydes in Flow

Executing photoredox reactions in flow offers solutions to frequently encountered issues regarding reproducibility, reaction time, and scale-up. Here, we report the transfer of a photoredox-catalyzed benzylic coupling of alkylarenes to aldehydes to a flow chemistry setting leading to improvements in terms of higher concentration, shorter residence times, better yields, ease of catalyst preparation, and enhanced substrate scope. Its applicability has been demonstrated by a multi-gram-scale reaction using high-power light-emitting diodes (LEDs), late-stage functionalization of selected active pharmaceutical ingredients (APIs), and also a photocatalyst recycling method.