Vanillylacetone supplier | CasNO.122-48-5

Name
Vanillylacetone
EINECS 204-548-3
CAS No. 122-48-5
Article Data43
CAS DataBase
Density 1.111 g/cm³
Solubility
Melting Point 40-41 °C(lit.)
Formula C₁₁H₁₄O₃
Boiling Point 323 °C at 760 mmHg
Molecular Weight 194.23
Flash Point 123.7 °C
Transport Information
Appearance Clear slightly yellow liquid.
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Zingiberone;Zingerone;NSC 15335;Gingerone;4-Hydroxy-3-methoxybenzylacetone;4-(4-Hydroxy-3-methoxyphenyl)-2-butanone;3-Methoxy-4-hydroxybenzylacetone;(4-Hydroxy-3-methoxyphenyl)ethylmethyl ketone;
PSA 46.53000
LogP 1.92240

Synthetic route

: 1080-12-2
Dehydrozingerone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With diphenyl sulfide; palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;	94%
With N-benzylammonium trifluoroacetate; 1,4-dihydro-2,6-dimethyl-3,5-bis<(methylamino)carbonyl>pyridine In tetrahydrofuran at 70℃; for 16h; Sealed tube;	93%
With palladium on activated charcoal; hydrogen; acetic acid In ethanol at 20℃; under 760.051 Torr;	87%

: 1080-12-2, 22214-42-2
(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With Rh/Al2O3; hydrogen In methanol at 20℃; under 750.075 Torr; for 2h;	100%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; for 4h; Time;	97%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;	97%

: 1080-12-2, 22214-42-2
(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

A: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

B: 39728-80-8
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Conditions

Conditions	Yield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen In methanol at 0 - 30℃; under 760.051 Torr; Reflux; Inert atmosphere;	A 98% B 2%
With diphenyl diselenide; hypophosphorous acid In glycerol at 90℃; for 0.5h; Inert atmosphere; chemoselective reaction;	A 68% B 19%
With hydrogen; palladium on activated charcoal In ethyl acetate

: 121-33-5
vanillin

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / aq. NaOH / 48 h / Ambient temperature 2: 43 percent / H2 / 10percent Pd/C / 3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: aq. NaOH 2: H2 / Pd-C / CHCl3 View Scheme
Multi-step reaction with 2 steps 1: aq. alkali 2: H2 / Raney-Ni View Scheme

: 4-((tert-butyldiphenylsilyl)oxy)-3-methoxybenzyl 3-oxobutanoate

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.75h;	70%

: 121-33-5
vanillin

iron (II)-chloride: iron (II)-chloride

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH / 20 °C 2: aq. HCl / 20 °C 3: H2; AcOH / Pd/C / ethanol View Scheme
Multi-step reaction with 2 steps 1: NaOH; water / 20 °C 2: H2 / Pd/C / ethyl acetate View Scheme
Multi-step reaction with 2 steps 1: 83 percent / NaOH / H2O / 3 h 2: H2 / 10 percent Pd/C / ethyl acetate View Scheme

: 1080-12-2
Dehydrozingerone

A: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

B: 39728-80-8
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 20℃; for 24h;	A 58% B 37%
With ethanol; palladium Hydrogenation;

: 78-94-4
methyl vinyl ketone

: 90-05-1
2-methoxy-phenol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With amberlyst-15 In toluene at 20 - 40℃;	36.6%

: C18H19O3Pol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; solid phase reaction;	12 mg

: 61152-59-8
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / 20 °C 2: H2; AcOH / Pd/C / ethanol View Scheme

: 39886-78-7
4-[4-(benzyloxy)-3-methoxyphenyl]butan-2-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol

: 911682-18-3
4-(4-((tert-butyldimethylsiloxy)-methyl)-3-methoxyphenyl)-but-3-ene-2-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium fluoride / tetrahydrofuran 2: H2 / Pd/C View Scheme

: 458-36-6
trans-coniferyl aldehyde

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: imidazole 2: MnO2 / pentane 3: tetrabutylammonium fluoride / tetrahydrofuran 4: H2 / Pd/C View Scheme

: 290820-47-2
(2E)-3-[4-[[tert-butyldimethylsilyl]oxy]-3-methoxyphenyl]acrylaldehyde

MeMgX: MeMgX

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: MnO2 / pentane 2: tetrabutylammonium fluoride / tetrahydrofuran 3: H2 / Pd/C View Scheme

: 911682-17-2
4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-but-3-en-2-ol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: MnO2 / pentane 2: tetrabutylammonium fluoride / tetrahydrofuran 3: H2 / Pd/C View Scheme

: 121-33-5
vanillin

KOH-solution: KOH-solution

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 10percent aq. sodium hydroxide / 96 h 2: 86 percent / H2 / Raney nickel / acetone View Scheme

: 2426-87-1
3-methoxy-4-(phenylmethoxy)benzaldehyde

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4 / methanol 2: PBr3 / diethyl ether 3: (i) nBuLi, THF, (ii) /BRN= 2130929/, (iii) aq. NaIO4, MeOH 4: H2 / Pd-C / methanol View Scheme

: 72724-00-6
1-(benzyloxy)-4-(bromomethyl)-2-methoxybenzene

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) nBuLi, THF, (ii) /BRN= 2130929/, (iii) aq. NaIO4, MeOH 2: H2 / Pd-C / methanol View Scheme

: 33693-48-0
4-benzyloxy-3-methoxybenzyl alcohol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: PBr3 / diethyl ether 2: (i) nBuLi, THF, (ii) /BRN= 2130929/, (iii) aq. NaIO4, MeOH 3: H2 / Pd-C / methanol View Scheme

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: thionyl chloride / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 3.1: trimethylaluminum / dichloromethane; toluene / 15 h / 20 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: tetrahydrofuran / -78 °C / Inert atmosphere 5.1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux 6.1: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr View Scheme

Yield

Multi-step reaction with 6 steps
1.1: thionyl chloride / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
3.1: trimethylaluminum / dichloromethane; toluene / 15 h / 20 °C / Inert atmosphere
3.2: 2 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / -78 °C / Inert atmosphere
5.1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux
6.1: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr
View Scheme

: (2E)-N-methoxy-3-[3-methoxy-4-(2-methoxyethoxymethoxy)phenyl]-N-methylacrylamide

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / -78 °C / Inert atmosphere 2: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux 3: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr View Scheme

: (3E)-4-[3-methoxy-4-(2-methoxyethoxymethoxy)phenyl]but-3-en-2-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux 2: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr View Scheme

: (2E)-1-(benzotriazol-1-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylaluminum / dichloromethane; toluene / 15 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: tetrahydrofuran / -78 °C / Inert atmosphere 4.1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux 5.1: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr View Scheme

Yield

Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
2.1: trimethylaluminum / dichloromethane; toluene / 15 h / 20 °C / Inert atmosphere
2.2: 2 h / 20 °C / Inert atmosphere
3.1: tetrahydrofuran / -78 °C / Inert atmosphere
4.1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux
5.1: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr
View Scheme

: (2E)-1-(benzotriazol-1-yl)-3-[3-methoxy-4-(2-methoxyethoxymethoxy)phenyl]prop-2-en-1-one

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trimethylaluminum / dichloromethane; toluene / 15 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: tetrahydrofuran / -78 °C / Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran; water / 5 h / Reflux 4.1: hydrogen; Rh/Al2O3 / methanol / 2 h / 20 °C / 750.08 Torr View Scheme

: (4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxyphenyl)methanol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap / toluene / Inert atmosphere; Reflux 2: zinc(II) chloride; tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 0.75 h / 20 °C View Scheme

: 69405-03-4
4-{[(tert-butyl)(diphenyl)silyl]oxy}-3-methoxybenzaldehyde

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / dichloromethane; ethanol / 0.75 h / 0 °C 2: dmap / toluene / Inert atmosphere; Reflux 3: zinc(II) chloride; tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 0.75 h / 20 °C View Scheme

: 121-33-5
vanillin

: 67-64-1
acetone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
Stage #1: vanillin; acetone With sodium hydroxide at 20℃; for 12h; Stage #2: With hydrogen

4-oxy-3-methoxy-benzylidenacetone: 4-oxy-3-methoxy-benzylidenacetone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With diethyl ether; hydrogen; platinum

: 89082-79-1
(E)-ethyl 2-(4-hydroxy-3-methoxybenzylidene)-3-oxo-butanoate

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With sodium hydroxide; sodium amalgam erwaermt man das Reaktionsprodukt mit konz. Natronlauge und erhitzt die erhaltene Saeure im Vakuum;

: 121-33-5
vanillin

: 67-63-0
isopropyl alcohol

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

Conditions

Conditions	Yield
With 1:1 copper and nickel alloy on γ-Al2O3 at 245℃; for 3h; Activation energy; Temperature; Reagent/catalyst; Inert atmosphere; Autoclave;	45.8%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 39728-80-8
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 2.5h; Solvent; Enzymatic reaction;	100%
With sodium tetrahydroborate In methanol at 20℃; for 1.5h;	96.6%
With sodium tetrahydroborate In ethanol	91%
With hydrogen; palladium on activated charcoal In ethyl acetate
Multi-step reaction with 2 steps 1: 84 percent / phenol, hexamethyldisilazane / benzene / Heating 2: 1.) lithium di-isopropylamide, hexanal, 2.) 2M HCl / 1.) -78 deg C, 1 h, THF, 2.) ether View Scheme

: 110-87-2
3,4-dihydro-2H-pyran

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 223801-42-1
4-(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 24h;	99%
With pyridinium p-toluenesulfonate In dichloromethane

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 2835-77-0
(2-aminophenyl)(phenyl)methanone

: 1408335-48-7
2-methoxy-4-((2-methyl-4-phenylquinolin-3-yl)methyl)phenol

Conditions

Conditions	Yield
With trifluoroacetic acid at 100℃; for 0.5h;	96%

: 112-31-2
caprinaldehyde

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 107257-18-1
5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one

Conditions

Conditions	Yield
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 6h;	95%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: caprinaldehyde In tetrahydrofuran at -78℃; for 3h; Time;	32%
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;

: 124-13-0
Octanal

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 77398-92-6
5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)dodecan-3-one

Conditions

Conditions	Yield
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 6h;	95%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: Octanal In tetrahydrofuran at -78℃; for 3h; Time;	32%
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 66-25-1
hexanal

: 23513-14-6, 72749-01-0, 74027-33-1, 39886-76-5
(+/-)-[6]-gingerol

Conditions

Conditions	Yield
With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 6h;	95%
With potassium tert-butylate In tetrahydrofuran at -78℃; for 1.5h;	76%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: hexanal In tetrahydrofuran at -78℃; for 3h; Time;	47%
With potassium tert-butylate In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;	30.73%
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃;

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 74-88-4
methyl iodide

: 6302-60-9
4-(3,4-dimethoxy-phenyl)-butan-2-one

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	95%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 1080-12-2, 22214-42-2
(E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one

Conditions

Conditions	Yield
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 9h; Sealed tube;	95%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 551-93-9
2-aminoacetophenone

: 1408335-47-6
4-((2,4-dimethylquinolin-3-yl)methyl)-2-methoxyphenol

Conditions

Conditions	Yield
With trifluoroacetic acid at 100℃; for 0.5h;	90%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 4-(3-aminobutyl)-2-methoxyphenol

Conditions

Conditions	Yield
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 15h;	89%
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; for 24h; chemoselective reaction;	87%
With ammonia; hydrogen In methanol at 90℃; under 15001.5 Torr; for 4h; Autoclave;	99 %Spectr.

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 719-59-5
2-Amino-5-chlorobenzophenone

: 1408335-50-1
4-((6-chloro-2-methyl-4-phenylquinolin-3-yl)methyl)-2-methoxyphenol

Conditions

Conditions	Yield
With trifluoroacetic acid at 100℃; for 0.5h;	86%

: 927-58-2
4-bromobutyroyl chloride

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 2-methoxy-4-(3-oxobutyl)phenyl 4-bromobutanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 13h;	85%

: 75-77-4
chloro-trimethyl-silane

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 56700-87-9
4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane; phenol In benzene Heating;	84%

: 31643-49-9
4-Nitrophthalonitrile

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 4-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere;	84%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 4301-14-8
acetylenemagnesium bromide

: 4-(3-hydroxy-3-methylpent-4-ynyl)-2-methoxyphenol

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;	84%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 66-25-1
hexanal

: 23513-13-5, 104186-09-6, 555-66-8
[6]-shogaol

Conditions

Conditions	Yield
With DIMCARB at 25℃;	80%
With DIMCARB at 20℃; for 72h;	55%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone With pyrrolidine In dichloromethane at 20℃; for 0.25h; Stage #2: hexanal In dichloromethane for 18h;	45.52 g

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 104-86-9
4-chlorobenzylamine

: 1247013-23-5
4-(3-(4-chlorobenzylamino)butyl)-2-methoxyphenol

Conditions

Conditions	Yield
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; 4-chlorobenzylamine In toluene for 16h; Reflux; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate In toluene at 0℃; for 16.5h; Reflux;	75%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; 4-chlorobenzylamine With sodium tetrahydroborate In toluene at 0℃; for 16h; Inert atmosphere; Dean-Stark; Reflux; Stage #2: With sodium tetrahydroborate In methanol; toluene for 16.5h; Reflux; Inert atmosphere;	75%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; 4-chlorobenzylamine In toluene for 16h; Reflux; Inert atmosphere; Dean-Stark; Stage #2: With sodium tetrahydroborate In methanol; toluene at 0℃; for 16.5h; Reflux;	75%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 3300-51-4
p-Trifluoromethylbenzylamine

: 1247013-24-6
2-methoxy-4-(3-(4-(trifluoromethyl)benzylamino)butyl)phenol

Conditions

Conditions	Yield
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; p-Trifluoromethylbenzylamine In toluene for 16h; Reflux; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate In toluene at 0℃; for 16.5h; Reflux;	74%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; p-Trifluoromethylbenzylamine In toluene at 0℃; for 16h; Inert atmosphere; Reflux; Dean-Stark; Stage #2: With sodium tetrahydroborate In methanol; toluene for 16.5h; Reflux; Inert atmosphere;	74%
Stage #1: 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; p-Trifluoromethylbenzylamine In toluene for 16h; Reflux; Inert atmosphere; Dean-Stark; Stage #2: With sodium tetrahydroborate In methanol; toluene at 0℃; for 16.5h; Reflux;	74%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 51762-67-5
3-nitrobenzene-1,2-dicarbonitrile

: 3-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere;	72%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 1775-95-7
2-amino-5-nitrobenzophenone

: 1408335-49-8
2-methoxy-4-((2-methyl-6-nitro-4-phenylquinolin-3-yl)methyl)phenol

Conditions

Conditions	Yield
With trifluoroacetic acid at 100℃; for 1.5h;	70%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 80638-48-8
3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde

: 79067-88-2, 81569-02-0, 128700-97-0
(E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-hepten-3-one

Conditions

Conditions	Yield
With DIMCARB at 20℃; for 96h;	70%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 139152-08-2
4,5-dichlorophthalonitrile

: 4,5-bis[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 48h; Inert atmosphere;	68%

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 1112137-79-7
4,4'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(butan-2-one)

Conditions

Conditions	Yield
With methyltri(butyl)ammonium permanganate In dichloromethane at 20℃;	65%
With methyltri(butyl)ammonium permanganate In dichloromethane at 20℃; for 1h; Inert atmosphere;	65%
With MTBAP In dichloromethane at 20℃; for 1h;
With Colletotrichum gloeosporioides In water; dimethyl sulfoxide at 20℃; for 360h; Microbiological reaction;

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: 139-85-5
3,4-dihydroxybenzaldehyde

: 1443545-73-0
(E)-1-(3,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-pent-1-en-3-one

Conditions

Conditions	Yield
With pyrrolidine; acetic acid In tetrahydrofuran Reflux;	63%

: 6479-18-1
1-methyl-2(1H)-quinoxalinone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: (Z)-3-(4-(4-hydroxy-3-methoxyphenyl)-2-oxobutylidene)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

Conditions

Conditions	Yield
With Amberlyst15; air In water at 20℃; for 24h; Irradiation; Green chemistry;	60%
With methanesulfonic acid In acetonitrile at 20℃; for 0.25h; Irradiation;	52%

: 6479-18-1
1-methyl-2(1H)-quinoxalinone

: 122-48-5
4-(4-hydroxy-3-methoxyphenyl)-2-butanone

: C20H20N2O4

Conditions

Conditions	Yield
With phosphoric acid In acetonitrile at 20℃; for 12h; Irradiation;	60%

Vanillylacetone Chemical Properties

Product Name: Vanillyl acetone (122-48-5)

Molecular Formula: C₁₁H₁₄O₃
Molecular Weight: 194.23g/mol
Mol File: 122-48-5.mol
Einecs: 204-548-3
Melting Point: 40-41 °C(lit.)
Boiling point: 141 °C0.5 mm Hg(lit.)
Flash Point: >230 °F
Density: 1.14 g/mL at 25 °C(lit.)
Refractive index: n20/D 1.541(lit.)
Product Categories: Miscellaneous Natural Products
Synonyms of Vanillyl acetone (122-48-5): (0)-paradol ; [0]-Paradol ; 3-Methoxy-4-hydroxybenzylacetone ; 3-methoxy-4-hydroxy-benzylacetone ; 4-(3-methoxy-4-hydroxyphenyl)-2-butanone ; 4-(4-hydroxy-3 ; 4-(4-hydroxy-3-methoxyphenyl)-2-butanon ; Gingerone .

Vanillylacetone Toxicity Data With Reference

Moderately toxic by ingestion. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.
rat	LD50	oral	2580mg/kg (2580mg/kg)		Food and Chemical Toxicology. Vol. 20, Pg. 851, 1982.

Vanillylacetone Consensus Reports

Reported in EPA TSCA Inventory.

Vanillylacetone Safety Profile

Safety Information of Vanillyl acetone (122-48-5):
Risk Statements: 36/37/38
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing

Vanillylacetone Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

Product Name

Vanillylacetone

Synthetic route

Vanillylacetone Chemical Properties

Vanillylacetone Toxicity Data With Reference

Vanillylacetone Consensus Reports

Vanillylacetone Safety Profile

Vanillylacetone Standards and Recommendations

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