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Cas:3128-07-2
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inquiryProduct Name: 5-ACETYLVALERIC ACID Synonyms: 6-oxoheptanoate;6-Oxoheptanoic acid 98%;5-Acetylvaleric acid, 97%, 97%;5-Acetylpentanoic acid, 6-Oxoenanthic acid;5-Acetylvaleric acid, 90+%, technical;5-Acetylpentanoic acid;6-Ketoenanthic acid;5-Acety
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inquiryConditions | Yield |
---|---|
With tropylium tetrafluoroborate; water In neat (no solvent) at 100℃; for 16h; Solvent; Temperature; Reagent/catalyst; Claisen Condensation; Inert atmosphere; | 99% |
With iron(III) chloride; water at 80℃; for 16h; Neat (no solvent); | 95% |
With indium(III) triflate; 2,6-di-tert-butyl-pyridine; water at 80℃; for 24h; Neat (no solvent); Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With oxygen; acetic acid In water at 60℃; under 750.075 Torr; for 8h; | 98% |
With oxygen; H7*10H2O In water at 60℃; under 750.06 Torr; for 8h; | 97% |
With oxygen; H6[PMo9V3O40]*11H2O In methanol at 60℃; under 750.06 Torr; for 24h; Product distribution; Kinetics; Further Variations:; Catalysts; Reagents; Solvents; Temperatures; reaction times; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; 12-tungstophosphoric acid/Al/C In tert-butyl alcohol at 60℃; for 24h; | 96% |
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In tert-butyl alcohol for 24h; Heating; | 90% |
With tert.-butylhydroperoxide; indium(III) chloride In water at 90℃; for 8.2h; | 84% |
Conditions | Yield |
---|---|
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In tert-butyl alcohol for 24h; Heating; | 95% |
With potassium permanganate; acetone at 0℃; | |
With dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 24h; | 91 %Chromat. |
trans-1-methylcyclohexane-1,2-diol
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h; | 93% |
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h; other 1,2-diols, other catalysts; | 93% |
With potassium carbonate at 20℃; for 3.3h; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A; | 70% |
hept-6-ynoic acid
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With [RhCl2(p-cymene)]2; water at 20℃; for 12h; | 88% |
With platinum catalyst In water at 37℃; for 96h; | 58% |
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With iron(III) chloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Green chemistry; | 75% |
1-trimethylsilyloxy-2-methyl-1-cyclohexene
A
6-oxoheptanoic acid
B
2-hydroxy-2-methylcyclohexanone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; titanium silicate for 24h; Heating; | A 73% B 6% |
Conditions | Yield |
---|---|
With ozone In neat (no solvent) at 20℃; for 5h; UV-irradiation; | A 70% B 10% |
Conditions | Yield |
---|---|
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; chemoselective reaction; | 69% |
With dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 24h; |
(1R,2R)-1-methylcyclohexane-1,2-diol
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; bis(acetylacetonato)dioxidomolybdenum(VI) In chlorobenzene at 60℃; for 24h; | 62% |
percarbonate de O,O-tert-butyle et O-isopropyle
butyric acid
6-oxoheptanoic acid
Conditions | Yield |
---|---|
at 130℃; for 2.5h; | 54% |
2-Methylcyclohexanol
A
6-oxoheptanoic acid
B
2-methylhexane-1,6-dioic acid
Conditions | Yield |
---|---|
With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h; | A 52% B 14% |
Conditions | Yield |
---|---|
With sulfuric acid | 24% |
With chromium(VI) oxide; sulfuric acid at 30℃; |
1-acetoxy-2-methylcyclohexene
A
6-oxoheptanoic acid
B
2-methyl-2-nitrocyclohexan-1-one
Conditions | Yield |
---|---|
With nitric acid; acetic anhydride at 15 - 22℃; for 2h; | A 17.3% B 21% |
(Z)-Cyclooctene
A
Adipic acid
B
heptanedioic acid
C
octane-1,8-dioic acid
D
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos In water at 85℃; for 7h; Further byproducts given; | A 7% B 2.6% C 24 % Chromat. D 4% |
1-methylcyclohex-1-ene
A
1,5-pentanedioic acid
B
Adipic acid
C
6-oxoheptanoic acid
D
5-ketohexanoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos In water at 85℃; for 6h; Yield given; Further byproducts given; | A 0.4% B 0.3% C n/a D 0.5% |
ethyl 6-chloro-6-oxohexanoate
sodium diethylmalonate
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With toluene Kochen des Reaktionsprodukts mit 20prozentig. HCl; |
1-ethynyl-2-methyl-cyclohexene
6-oxoheptanoic acid
Conditions | Yield |
---|---|
Ozonolyse; |
ethylmagnesium bromide
2-ethoxycarbonyl-1-cyclopentanone
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With diethyl ether Erwaermen des Reaktionsgemisches mit Acetylchlorid und Erhitzen des Reaktionsprodukts mit wss. Natriumcarbonat-Loesung; |
Conditions | Yield |
---|---|
Verseifung; |
Conditions | Yield |
---|---|
(i) H2, Pd-C, (ii) KOH, MeOH, (iii) H2SO4, CrO3; Multistep reaction; |
diethyl 2-acetylhexanedioate
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
carbon dioxide
2-(4-chlorobutyl)-2-methyl[1,3]dioxolane
6-oxoheptanoic acid
Conditions | Yield |
---|---|
(i) Mg, THF, (ii) /BRN= 1900390/, Et2O, (iii) aq. HCl; Multistep reaction; |
(E)-2-Diethylamino-7-oxo-oct-2-enenitrile
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
1-Methyl-2-methylselanyl-cyclohexene
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran |
formic acid
1-hexen-5-one
A
6-oxoheptanoic acid
B
α-methyl-δ-oxocaproic acid
Conditions | Yield |
---|---|
With carbon monoxide; palladium on activated charcoal; 1,4-di(diphenylphosphino)-butane In 1,2-dimethoxyethane at 150℃; under 5168 Torr; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
1-methylcyclohex-1-ene
A
1,5-pentanedioic acid
B
6-oxoheptanoic acid
C
6-oxoheptanal
D
n-hexan-2-one
E
5-ketohexanoic acid
F
Glutaraldehyde
Conditions | Yield |
---|---|
With ozone at 30℃; Mechanism; Product distribution; multistep reaction; |
2-methyl-2-decene
A
6-oxoheptanoic acid
B
2-hydroxy-2-methylcyclohexanone
Conditions | Yield |
---|---|
With cobalt(II); oxygen; 2-Methylcyclohexanone |
Conditions | Yield |
---|---|
iron(III) chloride | 100% |
With sulfuric acid In 1,2-dichloro-ethane Fisher esterification; | 100% |
With sulfuric acid In 1,2-dichloro-ethane for 12h; Heating; | 100% |
Conditions | Yield |
---|---|
Stage #1: 6-oxoheptanoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 23℃; for 0.25h; Stage #2: methyl iodide In acetone for 1h; | 95% |
Conditions | Yield |
---|---|
With phenylsilane; C9H8FeN2O8S2 In neat (no solvent) at 100℃; for 20h; Schlenk technique; Inert atmosphere; Glovebox; Irradiation; | 92% |
Conditions | Yield |
---|---|
In dichloromethane for 96h; Ambient temperature; | 90% |
6-oxoheptanoic acid
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane | 90% |
Conditions | Yield |
---|---|
With phenylsilane; C9H8FeN2O8S2 In neat (no solvent) at 100℃; for 20h; Schlenk technique; Inert atmosphere; Glovebox; Irradiation; | 90% |
6-oxoheptanoic acid
dicyclohexyl-carbodiimide
4-(tri-n-butylstannyl)-but-3-en-1-ol
4-(tri-n-butylstannyl)-3(E)-butenyl 6-oxoheptanoate
Conditions | Yield |
---|---|
In dichloromethane catalyst: (dimethylamino)pyridine, stirred at room temp. for 2 days; filtrated, concd., chromy. (silica gel, hexane/EtOAc), elem. anal.; | 89% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran for 8h; Ambient temperature; | 87% |
With dicyclohexyl-carbodiimide In tetrahydrofuran | 70% |
6-oxoheptanoic acid
4-trifluoromethylphenylamine
6-oxo-N-<4-(trifluoromethyl)phenyl>heptanamide
Conditions | Yield |
---|---|
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran | 86% |
With 4-methyl-morpholine; isobutyl chloroformate 1.) THF, -15 deg C, 15 min, 2.) THF, RT, overnight; Yield given. Multistep reaction; |
6-oxoheptanoic acid
heptane-1,6-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | 85% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 81% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere; | 70% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique; | 35% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
6-oxoheptanoic acid
4-butoxy-benzoic acid N-(4-methoxy-phenyl)-hydrazide
Conditions | Yield |
---|---|
With acetic acid at 80℃; for 2h; | 84% |
With acetic acid |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; | 84% |
6-oxoheptanoic acid
Propargylamine
6-oxo-N-(prop-2-yn-1-yl)heptanamide
Conditions | Yield |
---|---|
Stage #1: 6-oxoheptanoic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.25h; Substitution; Stage #2: Propargylamine In tetrahydrofuran at 20℃; for 0.5h; Substitution; | 80% |
With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; for 0.5h; | 80% |
Stage #1: 6-oxoheptanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0333333h; Stage #2: With benzotriazol-1-ol In dichloromethane for 0.0333333h; Stage #3: Propargylamine In dichloromethane at 20℃; for 16h; | 52% |
Conditions | Yield |
---|---|
Stage #1: 6-oxoheptanoic acid With thionyl chloride In N,N-dimethyl-formamide at 30℃; for 1h; Stage #2: 2-Phenoxyethanol In pentane at 20℃; for 1h; | 80% |
Conditions | Yield |
---|---|
In benzene at 50℃; for 1h; | 79.7% |
6-oxoheptanoic acid
5-(3-methyl-3H-diazirin-3-yl)pentanoic acid
Conditions | Yield |
---|---|
Stage #1: 6-oxoheptanoic acid With ammonia; hydroxylamine-O-sulfonic acid at -75 - 20℃; for 12h; Sealed tube; Stage #2: With potassium tert-butylate at -75 - 20℃; for 2h; Sealed tube; | 79% |
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / ammonia / 12 h / -78 - 20 °C / Sealed tube; liquid NH3 2: potassium hydroxide / ammonia / 2 h / -78 - 20 °C / Sealed tube; liquid NH3 View Scheme |
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In hexanes; dimethyl sulfoxide at 0 - 20℃; for 1h; Wittig Reaction; Stage #2: 6-oxoheptanoic acid With n-butyllithium In tetrahydrofuran; hexanes; dimethyl sulfoxide at 20℃; for 48h; Stage #3: With hydrogenchloride; water more than 3 stages; | 78% |
6-oxoheptanoic acid
Methyltriphenylphosphonium bromide
6-methyl-hept-6-enoic acid
Conditions | Yield |
---|---|
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In hexane; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 6-oxoheptanoic acid With n-butyllithium In tetrahydrofuran; hexane; dimethyl sulfoxide at 20℃; for 48h; Wittig olefination; Further stages.; | 78% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In hexanes; dimethyl sulfoxide at 0 - 20℃; for 1h; Stage #2: 6-oxoheptanoic acid In tetrahydrofuran; hexanes; dimethyl sulfoxide at 40℃; for 48h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes; dimethyl sulfoxide | 78% |
Conditions | Yield |
---|---|
Stage #1: sodium cyanide; 6-oxoheptanoic acid With sodium carbonate; hydrazinium sulfate In water for 44h; Stage #2: With hydrogenchloride In water Stage #3: With bromine In water for 1h; | 78% |
6-oxoheptanoic acid
ethanol
2-bromophenylhydrazine hydrochloride
ethyl 4-(7-bromo-2-methyl-1H-indol-3-yl)butanoate
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 1.5h; Fischer Indole Synthesis; | 76% |
Stage #1: 6-oxoheptanoic acid; 2-bromophenylhydrazine hydrochloride In ethanol at 50℃; for 0.666667h; Stage #2: ethanol With sulfuric acid for 16h; Reflux; | 15 g |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutylammomium bromide In acetone at 120℃; under 33753.4 Torr; for 0.5h; Inert atmosphere; Microwave irradiation; | 75% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 2h; | 74% |
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