Methyl mesityl ketone

Figure 5 Grignard reagent obtained from the reaction of mesityl methyl ketone and ethylmagnesium bromide.

Furfural reacts with ketones to form strong, crosslinked resins of technical interest in the former Soviet Union the U.S. Air Force has also shown some interest (42,43). The so-called furfurylidene acetone monomer, a mixture of 2-furfurylidene methyl ketone [623-15-4] (1 )> bis-(2-furfurylidene) ketone [886-77-1] (14), mesityl oxide, and other oligomers, is obtained by condensation of furfural and acetone under basic conditions (44,45). Treatment of the "monomer" with an acidic catalyst leads initially to polymer of low molecular weight and ultimately to cross-linked, black, insoluble, heat-resistant resin (46). 

The well-known condensation between 2-furaldehyde and acetone in a basic medium yields what is usually called furfurylidene acetone monomer composed of a mixture of 2-furfurylidene methyl ketone, di-2-furfurylidene ketone, mesityl oxide and other oligomers derived from further condensation reactions135. This mixture is then polymerized by the action of an acidic catalyst in the first phase of the reaction a polymer of low molecular weight is produced which on further treatment cross-links to a black insoluble and heat-resistant material136. ... 

In Scheme 8 40, the reaction of 9-anthryl trifluoromethyl ketone 103 and mesityl trifluoromethyl ketone 104 with catecholborane 106 in the presence of 10 mol% of chiral catalyst 107 (CBS) provides (R)-carbinol 108 and 109 with 94% and 100% ee, respectively. When methyl ketone instead of trifluoromethyl ketone is used in the reaction, product 110 is obtained with ( -configuration in 99.7% ee with over 95% yield. 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

Methylhydroxybenzene, see 2-Methylphenol p-Methylhydroxybenzene, see 4-Methylphenol Methylisoamyl acetate, see sec-Hexyl acetate Methyl isobutenyl ketone, see Mesityl oxide Methylisobutylcarbinol acetate, see sec-Hexyl acetate Methyl isobutyl ketone, see 4-Methyl-2-pentanone Methyl isocyanide, see Dimethylamine, Methyl isocyanate Methyl ketone, see Acetone... 

A. N-Nilroso-fi-methylaminoisobutyl methyl ketone. In a 2-1. three-necked flask, fitted with a mechanical stirrer, a thermometer, and a dropping funnel, is placed 250 ml. (2.1 moles) of 30% aqueous methylamine (Note 1). The flask is surrounded by an ice bath, and the stirrer is started. When the temperature of the solution has dropped to 5°, 196 g. (2 moles) of mesityl oxide is added through the dropping funnel at such a rate that the temperature remains below 20° (Notes 2 and 3). After the mesityl oxide has been added, the mixture is allowed to stand without cooling for 30 minutes. 

In the examples given the preparative value depends upon the ready availability of the required methyl ketone thus pinacolone (Expt 5.98), cyclopropyl methyl ketone (Expt 7.1) and mesityl oxide (Expt 5.213) are converted into 2,2-dimeth-ylpropanoic acid, cyclopropanecarboxylic acid and 3,3-dimethylacrylic acid respectively (Expts 5.124 and 5.125). 

The preparation of the requisite methyl ketone 67 starts from mesityl oxide (62) and hydroxylamine hydrochloride utilizing a known protocol (98BC1808) (Scheme 15). As correctly formulated in the original paper, hydroxylamine hydrochloride does not form the oxime but affords a low yield (11%) of the conjugate adduct, 4-(hydroxyamino)-4-methylpentan-2-one (63), which in solution is predominantly present as the hemiacetal cyclotautomer, 3,3,5-trimethylisoxazolidin-5-ol (64). Oxidation of 64 with mercuric oxide in chloroform furnishes a blue solution of 4-methyl-4-nitrosopentan-2-one (65) and its dimer 66 (ratio 85 15), which was isolated as colorless crystals 67 (54%). Condensation of nitroso ketone 65 with aniline in the presence of acetic acid provides / -phenyldiazenyl-a -methyl ketone 67 as a yellow oil (49%) (Scheme 15). 

Diazomethane (15, 3) Diazomethane and its homologs are prqrared by the action of sodium /jo-proporide in o-propyl alcohol upon the products of nitrosation from 8-alkyl3mino-iso-butyl methyl ketones (obtained by adding the amine to mesityl oxide). Adamson and Kenner, J. Chem. Soc. 1935, 286. 

Olefinic acids prepared by this method include y0,yS-dimethylacrylic acid (53%) from mesityl oxide, cinnamalacetic acid (70%) from cinnamal-acetone, and tra s-a-alkylcinnamic acids from the corresponding methyl ketones (80%). ... 

Certain N-nitroso derivatives are important intermediates in the synthesis of diazomethane and homologs. One synthesis involves the nitrosation of a /3-alkylaminoisobutyl methyl ketone the corresponding N-nitrosoamine is readily decomposed to the diazoalkane and mesityl oxide by treatment with sodium isopropoxide. ... 

Pinacolone (rert-butyl methyl ketone) is transformed into pivalic acid (trimethylacetic acid) in 71-74% yield [737], Mesityl oxide is converted into 3,3-dimethylacrylic acid in 49-53% yield [703], Isopropenyl methyl ketone gives methacrylic acid in 41% yield [697], and pregnenolone acetate furnishes 3-acetoxyetienic acid in 91-95% yield [117J] (equations 421-424). 

Two examples of the preparation of an acid by hypochlorite oxidation of a methyl ketone are 2-acetonaphthalene — /3-naphthoie acid" and mesityl oxide - dimethyl-acrylic acid."... 

Reaction with trialkylboranes. The reaction of trialkylborancs with acrolein (2, 15) and with methyl vinyl ketone (2. 284-185) yields, respectively, aldehydes and methyl ketones. However, the reaction is not directly applicable to all a,/3-unsaturated carbonyl compounds. Thus /ram-crotonaldehyde (I) and mesityl... 

The efficiency of a Raney nickel catalyst for hydrogenation of carbonyl groups is much diminished if the catalyst is treated with 0.1% acetic acid or an amino acid, particularly dibasic amino acids or L-phenylalanine but the efficiency for hydrogenation of C=C double bonds remains unaffected. Thus mesityl oxide was hydrogenated to isobutyl methyl ketone selectively and in good yield but cinnamaldehyde could not be reduced in this way.161 For asymmetric hydrogenation with Raney nickel modified by optically active 2-hydroxy carboxylic acids see Tatsumi et al.162... 

Oxidation of unsaturated ketones such as mesityl oxide, methyl vinyl ketone, isopropenyl methyl ketone, chalcone, and 2-cyclohexenone to the corresponding epoxides can also be effected by tert-butyl hydroperoxide in the presence of Triton B 50 and similar conditions have been used for epoxidation of [Pg.280]

An exchange resin sulfonic acid has also been used as catalyst in a very elegant ketone condensation Lorette948 obtained mesityl oxide in almost 80% yield by passing acetone vapors over Dowex 50 ethyl methyl ketone gives a mixture of the two isomers (5-methyl-4-hepten-3-one and 3,4-dimethyl-... 

Unsaturated acids can also be obtained in this way, by hypohalite oxidation of a,/ -unsaturated methyl ketones 3-methyl-2-butenoic acid has thus been obtained from mesityl oxide,136 and 5-phenyl-2,4-pentadienoic acid in 70% yield from cinnamylideneacetone 137... 

Ethyl-2-fluorobenzothiazolium tetra-fluoroborate, 223-225 Ethyl indolepropionates, 313-314 Ethyl ketals, 262 Ethyl lactate, 298 Ethyl lithioacetate, 225 Ethyl malonate, 311 Ethyl mandelate, 298 Ethyl mesityl ketone, 295 Ethyl methyl ketone, 340 N-Elhyl-5-phenylisoxazoiium 3 -sulfonate, 226... 

Isobutenyl methyl ketone. See Mesityl oxide 2-lsobutenyl-4-methyltetrahydropyran. See Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran... 

Methyl Akyl Acetate Methyl Isobutyl Ketone Mesityl Oxide Methyl Amyl Acetate Alpha-Methylstyrene N-Amyl Methyl Ketone Cresols... 

MESITYL OXIDE CHiCOCH> C(CH, 4-Mcthyl-3-penlcn>2Hme Isobulenyl methyl ketone. Methyl lso>hutenyl hetone, Iso-propyUdenc acetone Oxidizers S7 1.4 y... 

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