3-Ethyl-2-pentanone

Exercise 18-39 Show a synthesis of 3-ethyl-2-pentanone from ethyl 3-oxobutanoate. What advantage would this route have over alkylation of 2-pentanone with sodium amide and ethyl iodide (Section 17-4A.)... 

C7H14 5-methyl-trans-2-hexene 7385-82-2 361.26 30 594 1,2 11838 C7H140 3-ethyl-2-pentanone 6137-03-7 411.15 36.809 1.2... 

The relatively most frequent reaction is oxidation at the methinegroup giving tertiary alcohols as main products and secondary alcohols and ketones as minor products [902]. The hydroxylation occurs predominantly with retention of configuration [329, 620]. The oxidation of 3-ethylpentane with benzyltriethylammonium permanganate yields 24% of 3-ethyl-3-pen-tanol, 25% of 3-ethyl-2-pentanone, and 25% of 3-pentanone [902]. Under the same conditions, methylcyclohexane yields 72% of 1-methylcyclo-hexanol and 3% of 2-methylcyclohexanone [902]. 

Propose syntheses of the following ketones, beginning with ethyl 3-oxobutanoate (ethyl acetoac-etate). (a) 2-Hexanone (b) 2-octanone (c) 3-ethyl-2-pentanone (d) 4-phenyl-2-butanone. 

The cyclization of a-mercaptoketones with ammonium thiocyanate leads to the corresponding 2-mercaptothiazoles (144). For example, 2-mercapto-3-pentanone in ethereal solution with sulfuric acid gives 4-ethyl-5-methyl-2-mercaptothiazole (10), Ri = SH, R2 = Et, R3 = Me, when allowed to stand for 3 hr without heating with ammonium thiocyanate. 

Subsequently, Beals and Brown expanded the scope of the earlier work from their laboratory to include the tetraoxaquaterene derived from furan and 3-pentanone. Using 3,3-difurylpentane and diethyl ketone in the presence of dry hydrogen chloride gas, the all-ethyl analog of 6 (mp 249°) was obtained in 20% yield. ... 

A mixture of 22 parts of 1 -ethyl-1,4-dihydro-5H-tetrazol-5-one,45 parts of 1 -bromo-2-chloro-ethane,26 parts of sodium carbonate,0.3 part of potassium iodide and 240 partsof 4-methyl-2 pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The aqueous phase is extracted three times with dichloromethane. The combined organic phases are dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 28.4 parts (80%) of 1-(2-chloroethyi)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one as a residue. 

A mixture of 10 parts of 7-chloro-4-fluorobutyrophenone, 5.5 parts of 1-(1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinone, 4 parts of sodium carbonate, and 0.1 part of potassium iodide in 176 parts of 4-methyl-2-pentanone is stirred and refluxed for 64 hours. The cooled reaction mixture is filtered and the solvent is evaporated from the filtrate to leave an oily residue which is dissolved in toluene. The toluene solution is filtered and the solvent is evaporated. The resultant residue is recrystallized from a mixture of 32 parts of ethyl acetate and 32 parts of diisopropyl ether to give 1-[1-[(4-fluorobenzoyl)propyll-1,2,3,6-tetrahydro-4-pyridyl]-2-benzimidazolinone hydrate melting at about 145°-146.5°C. 

Chloro-4-pentanone N-Ethyl-N-2-hydroxyethy I amine 4,7-Dichloroquinoline Sulfuric acid... 

The 1-(N-ethyl-N-2-hydroxyethylamino)-4-pentanone from above (284.2 grams) was dissolved in 300 grams of 28% ammoniacal methanol and reduced catalytically with Raney nickel (at an initial pressure of 1,000 pounds) at room temperature. After 24 hours the catalyst was filtered off and the product distilled in vacuo through a column, yielding 254 grams of a fraction distilling at 88.5° to 96°C at 0.3 mm and comprising mainly 5-(N-ethyl-N-2-hydroxyethylamino)-2-pentylamine. An analytical sample of this fraction distilled at 93°C at 0.6 mm. 

We can use a ketone with two ethyl groups (3-pentanone) and allow it to react... 

Several of the synthetic efforts outlined in Section II were motivated partially by the necessity of increasing the processability of polyanhydrides. Solubilities of the 20 80 copolymers of P(CPP SA) and P(FAD SA) are compared by Domb and Maniar (1993). They reported improved solubility of the later over former in several organic solvents including (in order of decreasing solubility) THF, 2-butanone, 4-methyl-2-pentanone, acetone, and ethyl acetate. 

PENTANONE DIETHYL KETONE VALERALDEHYDE n-BUTYL FORMATE ETHYL PROPIONATE ISOBUTYL FORMATE ISOPROPYL ACETATE n-PROPYL ACETATE METHYL n-BUTYRATE... 

Fatty acids (oleic and linoleic acids) from resin acids Silicalite-1 Acetone, methyl ethyl ketone, 3-pentanone [178]... 

Synonyms AI3-01229 BRN 0605399 Caswell No. 574AA CCRIS 2052 EINECS 203-550-1 EPA pesticide chemical code 044105 Ethyl isobutyl ketone FEMA No. 2731 Elexanone Elex-one Isobutyl methyl ketone Isohexanone Isopropylacetone Methyl isobutyl ketone 2-Methyl-4-pentanone MIBK MIK NSC 5712 RCRA waste number U161 Shell MIBK UN 1245. 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

EINECS 203-468-6, see Ethylenediamine EINECS 203-470-7, see Allyl alcohol EINECS 203-472-8, see Chloroacetaldehyde EINECS 203-481-7, see Methyl formate EINECS 203-523-4, see 2-Methylpentane EINECS 203-528-1, see 2-Pentanone EINECS 203-544-9, see 1-Nitropropane EINECS 203-545-4, see Vinyl acetate EINECS 203-548-0, see 2,4-Dimethylpentane EINECS 203-550-1, see 4-Methyl-2-pentanone EINECS 203-558-5, see Diisopropylamine EINECS 203-560-6, see Isopropyl ether EINECS 203-561-1, see Isopropyl acetate EINECS 203-564-8, see Acetic anhydride EINECS 203-571-6, see Maleic anhydride EINECS 203-576-3, see m-Xylene EINECS 203-598-3, see Bis(2-chloroisopropyl) ether EINECS 203-604-4, see 1,3,5-Trimethylbenzene EINECS 203-608-6, see 1,3,5-Trichlorobenzene EINECS 203-620-1, see Diisobutyl ketone EINECS 203-621-7, see sec-Hexyl acetate EINECS 203-623-8, see Bromobenzene EINECS 203-624-3, see Methylcyclohexane EINECS 203-625-9, see Toluene EINECS 203-628-5, see Chlorobenzene EINECS 203-630-6, see Cyclohexanol EINECS 203-632-7, see Phenol EINECS 203-686-1, see Propyl acetate EINECS 203-692-4, see Pentane EINECS 203-694-5, see 1-Pentene EINECS 203-695-0, see cis-2-Pentene EINECS 203-699-2, see Butylamine EINECS 203-713-7, see Methyl cellosolve EINECS 203-714-2, see Methylal EINECS 203-716-3, see Diethylamine EINECS 203-721-0, see Ethyl formate EINECS 203-726-8, see Tetrahydrofuran EINECS 203-729-4, see Thiophene EINECS 203-767-1, see 2-Heptanone EINECS 203-772-9, see Methyl cellosolve acetate EINECS 203-777-6, see Hexane EINECS 203-799-6, see 2-Chloroethyl vinyl ether EINECS 203-804-1, see 2-Ethoxyethanol EINECS 203-806-2, see Cyclohexane EINECS 203-807-8, see Cyclohexene EINECS 203-809-9, see Pyridine EINECS 203-815-1, see Morpholine EINECS 203-839-2, see 2-Ethoxyethyl acetate EINECS 203-870-1, see Bis(2-chloroethyl) ether EINECS 203-892-1, see Octane EINECS 203-893-7, see 1-Octene EINECS 203-905-0, see 2-Butoxyethanol EINECS 203-913-4, see Nonane EINECS 203-920-2, see Bis(2-chloroethoxy)methane EINECS 203-967-9, see Dodecane EINECS 204-066-3, see 2-Methylpropene EINECS 204-112-2, see Triphenyl phosphate EINECS 204-211-0, see Bis(2-ethylhexyl) phthalate EINECS 204-258-7, see l,3-Dichloro-5,5-dimethylhydantoin... 

Chloroethyl vinyl ether, 2-Chlorophenol, Cyclohexene, Dalapon-sodium. Diallate. 1,1-Dichloroethane, 2,3-Dimethylamine, Dimethylbutane, 1,4-Dioxane, Ethylamine, Ethyl ether, Erhvl sulfide. 2-Heptanone, Metaldehvde. 2-Methvlbutane. 2-Methvl-2-butene. 2-Methyl phenol, Nitromethane, 4-Nitrophenol, 2-Nitropropane, 1-Octene, 2-Pentanone, Phenol, Toluene, Triethylamine, Vinyl chloride, o-Xylene, m-Xylene Acetamide, see Acetonitrile, Acrylamide, Acrylonitrile, Ethylamine... 

Ethyl tert-butvl ether. Ethylene dibromide, Ethyl ether, Ethvl sulfide. 2-Heptanone, Methanol, 2-Methyl-1,3-butadiene, 2-Methvl-2-butene. Methyl chloride, Methylene chloride, Methyl iodide. Methyl mercaptan, 2-Methylphenol, Methyl sulfide. Monuron. Nitromethane, 2-Nitropropane, A-Nitrosodimethylamine, 1-Octene, 2-Pentanone, Propylene oxide, Styrene, Thiram, Toluene, Vinyl chloride, o-Xylene, tn-Xylene Formaldehyde cyanohydrin, see Acetontrile,... 

The short-tailed fmit bat, Carollia perspicillata, discriminates the odor of ripe from that of green bananas. Odor cocktails of banana odor components were distinguished from the whole odor of banana (Laska, 1990). The two most common esters of banana odor are isopentyl acetate and isobutyl acetate. Nearly all fruit odors contain ethyl acetate. Isopropyl acetate and 2-pentanone are characteristic of putrefying fruits. 

Vo and Zugenmaier (105) determined the pitch of cellulose tricarbanilate (CTC, D.P. = 100) in 2-pentanone and methyl ethyl ketone (MEK) and ethyl cellulose (EC) in glacial acetic acid as a function of temperature, concentration, solvent, and degree of polymerization. The pitch of the helicoidal structure of CTC/MEK and CTC/2-pentanone is right-handed but EC in glacial acetic acid is left-handed. This is the first report that the substituent will influence the sense of the cholesteric superhelicoidal structure. 

Synonyms 2-Pentanone ethyl acetone Physical Form. Colorless liquid Uses. Solvent Exposure. Inhalation... 

The activated Ba(OH)2 catalyst was successfully used for the Michael reactions of chalcone with active methylene compounds 290), as well as for the Michael reaction of other benzylidene derivatives of acetone, butanone, 3-methylbutanone, 4-methyl-2-pentanone, and 3,3-dimethylbutanone with ethyl acetoacetate and diethyl malonate. The reaction with diethyl malonate gave good yields of the Michael adduct (between 65 and 93%), whereas with ethyl acetoacetate various products were obtained, depending on temperature and amount of catalyst (Scheme 43) 291). Thus, by varying the reaction conditions, it was possible to obtain a single product with practically 100% selectivity, the yields being higher than those obtained with soluble catalysts, such as KOH, NaOH, or piperidine. 

The reaction of ethyl A-arylcarbamates 3 with l-bromo-3,3-dimethyl-2-buta-none or l-bromo-3-ethyl-3-methyl-2-pentanone 4 in the presence of lithium bis(trimethylsilyl)amide (LiHMDS) results in the one-step synthesis of 3-aryl-5-ferf-butyl-2(3/T)-oxazolones 7 in fair to good yields (Fig. 5.2 Table 5.1, Fig. 5.3). This method is efficient for the preparation of bulky 5-substimted-2(37f)-oxazo-lones. 

Unter Aufnahme von molekularem Stickstoff und Bildung von Amino-Gruppen aus die-sem Stickstoff verlauft die Umsetzung von in situ erzeugtem Titanocen mit sauerstoff-freiem Stickstoff und (danach) z. B. 3-Pentanon nach der Hydrolyse erhalt man ein 2 1-Gemisch von 3-Amino-pentan und Bis-[]-ethyl-propyl]-amin in 25-50%iger Ausbeute (bez. auf aufgenommenen Stickstoff)2 ... 

In an apparatus suitably protected against atmospheric moisture and fitted with a gas-inlet tube, mechanical stirrer, and an efficient reflux condenser, to a solution of 45 gm (0.45 mole) of ethyl isopropyl ketone and 5 gm of freshly distilled acetyl chloride is added, through the gas-inlet tube, 18 gm (0.24 mole) of ethyl nitrite at 45°-55°C over a 2 hr period. The reaction mixture is stored overnight in a refrigerator, whereupon 15.2 gm (48.7% based on ethyl nitrite used) of 2-methyl-2-nitroso-3-pentanone dimer (bimolecular ethyl a-nitroso-isopropyl ketone) deposits. The product is isolated by filtration, m.p. 122°-123°C. 

The mother liquor is cooled in an ice bath and shaken with 40 ml of a cold 10% aqueous solution of sodium hydroxide. Thereupon 9 gm of a nonaqueous upper layer is separated and discarded. The aqueous layer is extracted with ether and the ether extract is discarded. The aqueous layer is then cooled in an ice bath and acidified to a pH of 7 with dilute sulfuric acid. The precipitate which forms is filtered and washed with water. This precipitate represents 5.7 gm (18 % based on ethyl nitrite used) of 2-methyl-4-oximino-3-pentanone, m.p. 92°-93°C. 

---