Cyclohexanone ethylene acetal

Oxidmion of ketone acetals and ethers. Ketones can be regenerated from the ethylene acetal derivatives by treatment with trityl fluoroborate in dry dichloro-methanc (Nj) at room temperature. Thus the reaction of trityl fluoroborate with cyclohexanone ethylene acetal results in cyclohexanone (80%) and triphenylmethane. The reaction thus involves hydride transfer to the triphenyl carbonium ions. Triethyl-oxonium fluoroborate can also be used but is somewhat less effective than trityl fluoroborate. 

The sugar (100 mg) is suspended in toluene (20/il), cyclohexanone ethylene acetal (700/il) and a drop of concentrated sulphuric acid, and the mixture is refluxed for 6h, then neutralized with solid sodium bicarbonate, filtered and evaporated to dryness under reduced pressure. Analysis is by TLC using toluene/ethanol (9 I) as solvent ]26]. 

Two i.r. methods have shown marked conformational differences in the juilibria of 2-chIoro- and 2-bromo-cyclohexanone ethylene acetal. The former has 72-80 % equatorial halogen whereas the latter is 70-80% axial. In a u.v. and i.r. study of variously substituted 2,6-diarylidene-cyclopentanones and -cyclohexanones extended conjugation effects are apparent in that the v(C=0) frequency is linearly correlated with Hammett o substituent values. 

The formation and chemistry of dithioacetals of sugars have been reviewed. 4,6-Dichloro-4,6-dideoxy-D-gaIactose reacted with cyclohexanone ethylene acetal in the presence of an acid catalyst to give the acyclic derivative (48), which was converted into the corresponding 5-ulose. Treatment with base converted (48) into the 5,6-anhydro-derivative, which was hydrolysed to give the L-idose diacetal (49), presumably by way of a4,5-anhydro-D-glucose derivative. 

A systematic study of the effects of solvent on the reaction showed that for the first-order decomposition of the chlorosulfite the stereochemistry varies from complete retention in dioxane to complete inversion in toluene. Tetrahydropyran, tetrahydrofuran, dioxolane, ethylene chloride and ethylene bromide as solvents, in this order, led to decreasing degrees of retention. Saturated hydrocarbons, acetonitrile, cyclohexanone, thiophene, acetal and acetophenone as solvents led to low yields of predominantly, but not completely inverted chloride. The results are in accordance with the mechanistic scheme... 

The solid monoacelie acid complex (hygroscopic) can be made by saturating an ethylene chloride solution of acetic acid with boron trifluoride, Altering, and washing the precipitate with more solvent the liquid diacetic acid complex remains in solution. The solid complex is recommended for the acetylation of a ketone, such as cyclohexanone. Thus acetic acid is stirred in an ice bath and boron trifluoride... 

Crystals from methanol- mp 53% Sol in acetone, cyclohexanone. ethyl acetate, toluene, xylene, ethylene glycol -propylene glycol, some oils Practically insol in water. LDm in male, female rats 400, 330 mg/kg orally 790, 1250... 

GP-71-SS Mer pto Modfiled Silcone Fluid varnish remover Ben acetate Cyclohexane Cyclohexanone, Ethoxyelhanol acetate Ethylene Miloride Isopropyl ether, Mestyl oxide varnish resin Penlalyi A varnish thinner l r splits... 

Acid blue 9 Acid violet 49 Cyclohexanone Ethoxyethanol acetate Ethylene glycol Potassium dichromate stain, wood/biological materials Direct black 38... 

Benzyl acetate Cyclohexane Cyclohexanone Ethoxyethanol acetate Ethylene dichloride Isopropyl ether Mesityl oxide 1,2,3-Trichloropropane Tripropylene glycol varnish, under sealer coating Shellac varnishes... 

I whereupon 1 mole of Hg is I absorbed during 0.5 hr. -> 2-hydroxy-3-cyclohexanone-l-acetic acid ethylene ketal... 

Several cleaning formulations for specific uses contain unreacted polyamines. Examples include mixtures of ammonium alkylbenzenesulfonate, solvents, and PIP which give good cleaning and shine performance on mirrors and other hard surfaces without rinsing (305), and a hard-surface cleaner composed of a water-soluble vinyl acetate—vinyl alcohol copolymer, EDA, cyclohexanone [108-94-1] dimethyl sulfoxide [67-68-5] a surfactant, and water (306). TEPA, to which an average of 17 moles of ethylene oxide are added, improves the clay sod removal and sod antiredeposition properties of certain hquid laundry detergents (307). 

Cyclohexanone (0.52 g, 5.3 mmol) is added, under a nitrogen atmosphere, to a mixture of dry ethylene glycol (3 mb, 54 mmol) and dry methanol (20 mb). Tri-methylchlorosilane 14 (1.4 mb, 11 mmol) is added and the mixture stirred for 16 h at room temperature. The mixture is neutralized to pH 6 by addition of a 5% solution of sodium methoxide in methanol and the solvent is removed under reduced pressure. The residue is dissolved in 20 mb ether and filtered through 5 g silica gel, which is then washed with 2x10 mb ether. The combined ether eluates are evaporated and the crude residue submitted to flash chromatography on silica gel with ethyl acetate-hexane (1 10) to give 0.63 g (83%) cyclohexanoneethylene ketal 392 [28] (Scheme 5.87). 

Cyclohexanone is miscible with methanol, ethanol, acetone, benzene, ri-hexane. nitrobenzene, diethyl ether, naphtha, xylene, ethylene glycol, isoamy] acetate, dicthylamine, and most organic solvents. This ketone dissolves cellulose nitrate, acetate, and ethers, vinyl resins, raw rubber, waxes, fats, shellac, basic dyes, oils, lalex. bitumen, kaure. elemi. and many other organic compounds. 

Intermolecular Nucleophilic Substitution with Heteroatom Nucleophiles. A patent issued in 1965 claims substitution for fluoride on fluorobenzene-Cr(CO)3 in dimethyl sulfoxide (DMSO) by a long list of nucleophiles including alkoxides (from simple alcohols, cholesterol, ethylene glycol, pinacol, and dihydroxyacetone), carboxylates, amines, and carbanions (from triphenyhnethane, indene, cyclohexanone, acetone, cyclopentadiene, phenylacetylene, acetic acid, and propiolic acid). In the reaction of methoxide with halobenzene-Cr(CO)3, the fluorobenzene complex is ca. 2000 times more reactive than the chlorobenzene complex. The difference is taken as evidence for a rate-limiting attack on the arene ligand followed by fast loss of halide the concentration of the cyclohexadienyl anion complex does not build up. In the reaction of fluorobenzene-Cr(CO)3 with amine nucleophiles, the coordinated aniline product appears rapidly at 25 °C, and a carefiil mechanistic study suggests that the loss of halide is now rate limiting. 

Aromatic and aliphatic carbonyl compounds condense with glycols, such as ethylene, propylene, and trimethylene glycols, to form cyclic acetals p-toluenesulfonic acid has proved to be an excellent catalyst. As before, the water formed in these reactions is conveniently removed by an azeotropic distillation with benzene. Representative aldehydes and ketones that undergo this acetalization include acetone, cyclohexanone, pinacolone, acetophenone, benzophenone, n-heptaldehyde. 

Oxidation ethylene, cumene, butane, toluene, xylene, ethylbenzene, acetaldehyde, cyclohexane, cyclohexene, n-paraffins, glucose vinyl acetate, phenol, acetone, methyl ethyl ketone, benzoic acid, phthalic acid, acetophenone, acetic acid, acetic anhydride cyclohexanol and cyclohexanone, adipic acid, sec-alcohols, glutonic acid... 

Cyclohexanone Cyclohexyl Alcohol Diesel Fuels Dimethyl an nine DIoxane (p-) Epichlorohydrin Ethyl Acetate Ethylene Chloride... 

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