Heptanone oxidation

Tropolone has been made from 1,2-cycloheptanedione by bromination and reduction, and by reaction with A -bromosuccinimide from cyolo-heptanone by bromination, hydrolysis, and reduction from diethyl pimelate by acyloin condensation and bromination from cyclo-heptatriene by permanganate oxidation from 3,5-dihydroxybenzoic acid by a multistep synthesis from 2,3-dimethoxybenzoic acid by a multistep synthesis from tropone by chlorination and hydrolysis, by amination with hydrazine and hydrolysis, or by photooxidation followed by reduction with thiourea from cyclopentadiene and tetra-fluoroethylene and from cyclopentadiene and dichloroketene. - ... 

Methyl-2-pentene-2-one, see Mesityl oxide 4-Methyl-2-pentyl acetate, see sec-Hexyl acetate 4-Methyl-l-pentylene, see 4-Methyl-l-pentene Methyl pentyl ketone, see 2-Heptanone Methylpentylmethylene, see Methylcyclopentane a-Methylphenanthrene, see 1-Methylphenanthrene... 

UN 1206, see 3,3-Dimethylpentane Heptane UN 1208, see 2,2-Dimethylbutane, 2,3-Dimethylbutane, Hexane, 2-Methylpentane UN 1212, see Isobutyl alcohol UN 1213, see Isobutyl acetate UN 1218, see 2-Methyl-l,3-butadiene UN 1220, see Isopropyl acetate UN 1221, see Isopropylamine UN 1224, see 3-Heptanone, 2-Hexanone, Isophorone UN 1229, see Mesityl oxide UN 1230, see Methanol UN 1231, see Methyl acetate UN 1232, see 2-Butanone UN 1233, see sec-Hexyl acetate... 

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,... 

Propanal, see Acrolein, Allyl alcohol. 2-Heptanone, 2-Pentanone, 1-Octene Propanamide, Acrylamide 1,2-Propanediol, see 1-Pentene, Propylene oxide... 

Problem 15.14 Synthesize (a) p-methoxybenzaldehyde from benzene (b) cyclohexylethanal by hydrobora-tion and oxidation (c) phenylacetaldehyde, using 1,3-dithiane (d) phenyl n-propyl ketone from a dithiane (e) cyclohexyl phenyl ketone from PhCOOH and RLi (/) 2-heptanone, using a cuprate ... 

Mesityl oxide Methyl (n-amyl)ketone (2-heptanone)... 

In an analogous synthesis,23 3-butyI-l-heptyne was also characterized by mercuric oxide-sulfuric acid hydration4 to the known 3-butyl-2-heptanone,5 6 which also formed the known semicar-bazone.6... 

SAP catalysts have also been applied in the Wacker oxidation584 of higher olefins where the separation of products from the catalyst is cumbersome. Palladium(II) and copper(II) salts immobilized on controlled pore glass CPG-240 in the presence of water catalysed the oxidation of 1-heptene to 2-heptanone in conversions up to 24%.585 Significant isomerization to 2-heptene and 3-heptene (isomerization/oxidation=2/3) was also observed. However, an advantage of SAP-Wacker oxidation catalysts over classical systems is that the Cu(II) is confined to the support and therefore not corrosive whereas aqueous Cu2+ is very corrosive to steel. 

Ethyl N-benzylcarbamate and its nitroso compound have been prepared by methods similar to those described for ethyl N-methylcarbamate and its nitroso compound.2 3 2-Phenylcyclo-heptanone has been prepared by the reaction of ethyl N-nitroso-N-benzylcarbamate4 with cyclohexanone,5 by the reaction of phenyldiazomethane with cyclohexanone,6 by the reaction of ethyl N-nitroso-N-methyl carbamate with 2-phenylcyclohexa-none,6 and by the rearrangement of l-phenyl-2-cyclohexylethylene oxide.7... 

Two of these ketones, 2-heptanone and 2-octanone, have been identified among the thermal decomposition products of corn oil, and their quantities were found to increase when corn oil was oxidized in the presence of zein (4). The effect of an increased surface area for reaction between zein and corn oil during extrusion is hard to determine from these data. 

A stereoselective synthesis of 3-( 1,2,4-triazolo[4,3-A ]azin-3-yl)-bicyclo[2.2.1 ]heptanones 58 starting from (l/ )-(+)camphor 56 has been described. The reaction comprises oxidative cyclization of the intermediate hydrazones 57 with methanolic bromine <02TA821>. 

Amidone (6-dimethylamino-4,4-diphenyl-3-heptanone), while resistant to hydrogenation with Raney nickel, could be hydrogenated to the alcohol with platinum oxide as catalyst.140 However, isoamidone (6-dimethylamino-4,4-diphenyl-5-methyl-3-hexanone)(15, R = Me) did not absorb hydrogen in the presence of platinum oxide and the reduction to the corresponding alcohol was achieved by reduction with lithium aluminum hydride.141... 

TABLE 21. Concentrations (ppb in emuision) of 2-Heptanone Perceived to Have the Same Fiavor intensity as the Components isoiated from Commerciai Soybean Oii Oxidized at 35°C Under Fiuorescent Light for up to 11 Days (293). 

When 2-heptanone (950 mg kg was administered orally to rabbits, 40% of administered dose was excreted as heptyl-2-glucuronide, and traces of the unchanged ketone were also found in the urine. Compound undergoes carbonyl reduction to a secondary alcohol and co-l oxidation to a hydroxy-ketone which is further oxidized to 2,6-heptadione. 

Cyclic ketones. Diazomethane ring expansion of cyclohexanone gives cyclo-heptanone in yields as high as 63% and smaller amounts of cyclooctanone and methylenecyclohexane oxide. The cycloheptanone is easily separated from the... 

Cyclohexanones can be dehydrogenated to enones by treatment of the corresponding enol silanes with DDQ in the presence of a catalytic amount of the bis-silyl derivative of acetamide. However, the yields fall off drastically when the reaction is applied to cyclopentanones and cyclo-heptanones. Another new method for dehydrogenation of carbonyl compounds consists of conversion to their pyridine-2-sulfIde derivatives, followed by oxidation (MCPBA), and by mild heat. ... 

The reaction of 2-methyl-2-propenylmagnesium chloride with the allenic aldehyde 342 (from isobutyraldehyde and 2-methyl-3-butyn-2-ol) gave the precursor 343 for an internal [2 + 2] cycloaddition. After oxidation and irradiation, the bicyclo[3.2.0]heptanone 324 obtained was converted to ( )-lineatin [( )-... 

Another chiral vinylogous urethane, 677, played a central role in the synthesis of (- )-652 by Lhommet and co-workers (Scheme 90) 494). This compound, prepared from (/ )-a-methylbenzylamine (678) (495), was diastereoselectively hydrogenated over platinum oxide to give the amino-ester 679 (de >95%). More significantly, methylation of the anion of 679 under conditions of kinetic control afforded 680 (de ca 98%) in 33% overall yield from the chiral amine 496). Wittig reaction of the aldehyde derivative 681 with the stabilized ylide l-(triphenylphosphoranylidene)-2-heptanone yielded 682 (90%) as a 4 1 mixture of E and Z isomers. When this product... 

Table 6. Baeyer-Villiger oxidations of 7-oxabicyclo[2.2.1]heptanone derivatives with alpha oxygen substituentsa...

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