Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate for 0.0333333h; microwave irradiation; | 98% |
With iron(III) chloride for 0.0166667h; Friedel Crafts acylation; Microwave irradiation; regioselective reaction; | 98% |
With aluminum oxide; methanesulfonic acid at 120℃; for 0.333333h; | 85% |
Conditions | Yield |
---|---|
Stage #1: acetic anhydride; hydroquinone In 1,2-dichloro-ethane at 100℃; for 4h; Friedel-Crafts Acylation; Stage #2: With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 120℃; for 3h; | 92% |
zinc(II) chloride at 145 - 150℃; for 0.25h; | 76% |
Conditions | Yield |
---|---|
With ammonium persulfate; silver nitrate In water; acetonitrile at 70℃; for 2h; | 92% |
Conditions | Yield |
---|---|
for 0.116667h; Rearrangement; microwave irradiation; | 90% |
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h; Stage #2: With hydrogenchloride; water for 0.5h; Reflux; | 85% |
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 180℃; for 3h; Fries rearrangement; Stage #2: With hydrogenchloride In methanol Reflux; | 76.6% |
1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating; | 89% |
Dipropyl ether
benzene-1,4-diyl diacetate
A
2,5-Dihydroxyacetophenone
B
2-hydroxy-5-propoxyacetophenone
Conditions | Yield |
---|---|
With boron trifluoride for 1h; Fries rearrangement; Heating; | A 89% B 9% |
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate for 0.025h; microwave irradiation; | 85% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5h; Michael reaction; | A n/a B 80% C 17% |
In dichloromethane at 20℃; for 5h; Arylation; | A n/a B 51% C 17% |
2-Acetyl-1,4-benzoquinone
trimethyl(2-methyl-2-propenyl)stannane
A
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In benzene | A 6% B 77% |
Conditions | Yield |
---|---|
With boron dimethyl-trifluoro sulphide In dichloromethane at 20℃; for 1.5h; | 74% |
With carbon disulfide; aluminum tri-bromide | |
With pyridine hydrochloride |
Conditions | Yield |
---|---|
With aluminium trichloride at 140℃; for 2h; Fries rearrangement; | 71% |
Fries rearrangement; |
Conditions | Yield |
---|---|
With zinc at 47 - 48℃; for 0.0166667h; Friedel-Crafts acylation; microwave irradiation; | 70% |
With aluminium trichloride; nitrobenzene |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene for 3h; crossover Friess rearrangement; Heating; | 65% |
5'-cinnamyloxy-2'-hydroxyacetophenone
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
at 220℃; for 20h; | 64% |
2',5'-dimethoxyacetophenone
A
1-(2-hydroxy-5-methoxyphenyl)ethan-1-one
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With boron dimethyl-trifluoro sulphide In dichloromethane at 0℃; for 0.166667h; | A 64% B 27% |
2-Acetyl-1,4-benzoquinone
A
2-Acetyl-3-(3-acetyl-4-hydroxyphenoxy)-1,4-benzoquinone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With rose bengal In acetonitrile for 8h; Irradiation; Yields of byproduct given; | A 60% B n/a |
benzene-1,4-diyl diacetate
phenol
A
o-hydroxyacetophenone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation; | A 25% B 60% |
2-Acetyl-1,4-benzoquinone
A
5-hydroxy-2,3-dihydrobenzofuran-3-one
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In benzene for 72h; Irradiation; | A 50% B 45% |
In benzene for 72h; Mechanism; Irradiation; | A 50% B 45% |
α-naphthol
benzene-1,4-diyl diacetate
A
1-hydroxy-2-acetonaphthone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation; | A 20% B 50% |
benzene-1,4-diyl diacetate
β-naphthol
A
1-(2-hydroxy-1-naphthyl)ethan-1-one
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation; | A 35% B 45% |
3,5-dihydroxyphenol
benzene-1,4-diyl diacetate
A
2,4,6-trihydroxyacetophenone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene for 0.5h; cross Fries reaction; microwave irradiation; | A 35% B 40% |
2-Acetyl-1,4-benzoquinone
trimethyl(allyl)stannane
A
2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In benzene for 5h; | A 27% B 36% C 23% |
In benzene dissolved acylquinone and allylstannane stood for 5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.; | A 27% B 36% C 23% |
benzene-1,4-diyl diacetate
A
1,4-diacetyl-2,5-dihydroxybenzene
B
5'-Acetoxy-2'-hydroxyacetophenone
C
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In methanol for 12h; Irradiation; | A 10% B 15% C 35% |
acetophenone
A
3-Hydroxyacetophenone
B
2,3,6-trihydroxyacetophenone
C
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h; Mechanism; Product distribution; | A 31% B 4% C 18% |
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride at -35℃; for 0.5h; | A 31% B 4% C 18% |
4a,8a-cis-4a-acetyl-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With pyridine In xylene Heating; | 29% |
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In pyridine; xylene at 120℃; for 3h; | 29% |
2-Acetyl-1,4-benzoquinone
allyltributylstanane
A
2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In benzene for 1.5h; | A 29% B 10% C 10% |
In benzene dissolved acylquinone and allylstannane stood for 1.5 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.; | A 29% B 10% C 10% |
Conditions | Yield |
---|---|
With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide; dimethyl sulfoxide for 3h; Reflux; | 19% |
2-Acetyl-1,4-benzoquinone
trimethyl(allyl)stannane
A
2-acetyl-3-prop-2'-enyl-1,4-hydroquinone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
In acetonitrile dissolved acylquinone and allylstannane stood for 10 min under Ar; concentrated; column chromy. (silica gel); eluted (hexane/ether); NMR; IR; mass spectra; elem. anal.; | A 18% B 18% |
benzene-1,4-diyl diacetate
A
5'-Acetoxy-2'-hydroxyacetophenone
B
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With aluminium trichloride at 190 - 200℃; | |
Stage #1: benzene-1,4-diyl diacetate With aluminium trichloride; sodium chloride at 195℃; for 0.15h; Fries rearrangement; Stage #2: With hydrogenchloride In water for 12h; Further stages. Title compound not separated from byproducts.; | |
Stage #1: benzene-1,4-diyl diacetate With aluminum (III) chloride; sodium chloride at 140 - 195℃; for 0.15h; Stage #2: With hydrogenchloride; water |
ethyl (E)-4-methyl-3,5-hexadienoate
2,5-Dihydroxyacetophenone
(4aR,5R,8aS)-4a-Acetyl-5-(2-benzyloxy-ethyl)-6-methyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
Conditions | Yield |
---|---|
With silver(l) oxide Ambient temperature; Absence of light; | 100% |
Conditions | Yield |
---|---|
With silver(l) oxide Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver(l) oxide Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver(l) oxide for 72h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With silver(l) oxide for 168h; Ambient temperature; | 100% |
3,4-dihydro-2H-pyran
2,5-Dihydroxyacetophenone
1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; | 99% |
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h; | 91% |
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 5h; | 87% |
benzyl bromide
2,5-Dihydroxyacetophenone
1-[2',5'-bis(phenylmethoxy)phenyl]ethanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Etherification; Heating; | 99% |
With potassium carbonate In acetone for 24h; Reflux; | 94% |
Stage #1: 2,5-Dihydroxyacetophenone In 1,2-dimethoxyethane at 80℃; Inert atmosphere; Stage #2: benzyl bromide In 1,2-dimethoxyethane; N,N-dimethyl-formamide for 12h; | 93% |
Conditions | Yield |
---|---|
With kiwi juice In water at 20℃; for 0.0833333h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry; | 99% |
With lithium perchlorate for 0.0194444h; Irradiation; | 83% |
trimethylsilyl trifluoromethanesulfonate
2,5-Dihydroxyacetophenone
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -30 - -10℃; for 0.666667h; Inert atmosphere; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran 0 deg C to room temp., 0.5 to 1 h; | 98% |
Conditions | Yield |
---|---|
With lithium perchlorate; acetic acid In nitromethane for 16h; electrolysis; | 97% |
tert-butyldimethylsilyl chloride
2,5-Dihydroxyacetophenone
5'-t-butyldimethylsilyloxy-2'-hydroxyacetophenone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 12h; | 97% |
o-hydroxyacetophenone
2,5-Dihydroxyacetophenone
tert-butyl 4-oxo-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate
Conditions | Yield |
---|---|
With pyrrolidine In methanol for 24h; | 97% |
allyl bromide
2,5-Dihydroxyacetophenone
1-(5-allyloxy-2-hydroxyphenyl)-1-ethanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Heating; | 96% |
With potassium carbonate; sodium iodide In acetone for 15h; Heating; | 86% |
With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux; | 86% |
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane for 0.25h; Ambient temperature; | 95% |
With oxygen In chloroform; water at 20℃; under 760.051 Torr; for 6h; | 88% |
With cerium(IV) ammonium nitrate; silica gel In dichloromethane for 0.25h; | 84% |
benzyl bromide
2,5-Dihydroxyacetophenone
5-benzyloxy-2-hydroxyacetophenone
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate; potassium iodide In toluene at 115℃; for 14h; | 95% |
With potassium carbonate In acetone for 48h; Reflux; | 92% |
With sodium hydrogencarbonate In ethanol at 0 - 10℃; for 3.33333h; | 88.3% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 24h; Heating; | 95% |
6,10,14-trimethyl-5,9,13-pentadecatriene-2-on
2,5-Dihydroxyacetophenone
6-Hydroxy-2-methyl-2-((3E,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-chroman-4-one
Conditions | Yield |
---|---|
With pyrrolidine; 3 A molecular sieve In ethanol Heating; | 95% |
pivaloyl chloride
2,5-Dihydroxyacetophenone
2,2-dimethylpropanoic acid 2-acetyl-1,4-phenylene ester
Conditions | Yield |
---|---|
With pyridine at 20℃; | 95% |
With pyridine at 20℃; for 18h; |
orthoformic acid triethyl ester
2,5-Dihydroxyacetophenone
6-hydroxy-4-oxo-4H-1-benzopyran
Conditions | Yield |
---|---|
With perchloric acid In water at 20 - 100℃; for 1.08333h; | 95% |
With perchloric acid at 20℃; for 1.5h; | 78% |
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane at 0℃; Inert atmosphere; Reflux; | 94.9% |
2,5-Dihydroxyacetophenone
2-bromo-1-(2,5-dihydroxyphenyl)ethanone
Conditions | Yield |
---|---|
With aluminium trichloride; Montmorillonite K10; bromine In ethyl acetate at 20℃; for 2h; | 94% |
With urea-hydrogen peroxide; acetic acid; sodium bromide; silica gel at 120 - 122℃; for 0.00611111h; microwave irradiation; | 71% |
With copper(I) bromide In chloroform; ethyl acetate for 6h; Reflux; | 6% |
tert-butyldimethylsilyl chloride
2,5-Dihydroxyacetophenone
1-(2,5-bis(tert-butyldimethylsilyloxy)phenyl)ethanone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere; | 93.2% |
N-tert-butyloxycarbonylpiperidin-4-one
2,5-Dihydroxyacetophenone
tert-butyl 6-hydroxy-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate
Conditions | Yield |
---|---|
With pyrrolidine In methanol at 60℃; for 48h; | 93% |
With pyrrolidine In methanol for 18h; Reflux; | 87% |
With pyrrolidine In methanol for 23h; Reflux; | 82% |
6-Methyl-hept-5-en-2-on
2,5-Dihydroxyacetophenone
6-Hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-4-chromanon
Conditions | Yield |
---|---|
With pyrrolidine; 3 A molecular sieve In ethanol Heating; | 92% |
2,5-Dihydroxyacetophenone
benzylamine
2,5-Dihydroxyphenylethylidenebenzylamine
Conditions | Yield |
---|---|
In toluene Heating; or ZnCl2, 1) 30 min, 160 deg C, 2) 5 min, 180 deg C; | 92% |
In toluene Heating; | 90% |
Conditions | Yield |
---|---|
With piperidine for 0.166667h; Neat (no solvent); Microwave irradiation; | 92% |
With pyrrolidine In ethanol Reflux; | 92% |
With Amberlite IRA 400 basic resin for 0.133333h; Microwave irradiation; Neat (no solvent); | 86% |
With pyrrolidine In isopropyl alcohol for 2h; Mechanism; Heating; other acetophenones; | 72% |
With pyrrolidine In isopropyl alcohol for 2h; Heating; | 72% |
1. | ipr-mus LDLo:500 mg/kg | CBCCT* “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 5 (1953),140. |
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