R-Butyl alcohol

Simple ketones and esters are inert. On the other hand, nitroalkanes react smoothly in r-butyl alcohol as a solvent with butadiene, and their acidic hydrogens are displaced with the octadienyl group. From nitromethane, three products, 64, 65, and 66, are formed, accompanied by 3-substituted 1,7-octadiene as a minor product. Hydrogenation of 65 affords a fatty amine 67 which has a primary amino function at the center of the long linear chain[46,61]. 

The addition of primary and secondary alcohols proceeds not only in the presence of acid but also in neutral solution (62JCS1591, 65JCS6930, 71JCS(B)2423). Stable 1 1 mono- and 2 1 di-(T-adducts were found and characterized spectrally, r-Butyl alcohol does not form adducts for steric reasons. 

CHjBr with potassium t-butoxide in r-butyl alcohol... 

In this example, sodium in r-butyl alcohol cleaves two aryl benzyl ethers and reduces a double bond that is conjugated with an aromatic ring non-conjugated double bonds are stable. 

A 500-mI, three-necked, round-bottom flask is fitted with a condenser, a thermometer, and a mechanical stirrer all openings are protected by drying tubes. In the flask is placed a mixture of 61.2 g (0.61 mole) of acetic anhydride and 27 g (about 0.4 mole) of finely pulverized calcium carbide, and the mixture is refluxed for 2 hours. After cooling to 70°, 29.6 g (0.4 mole) of dry r-butyl alcohol is added and the mixture is refluxed for 4 days with continuous stirring. The mixture is cooled and the thick slurry is decomposed by careful addition to ice, followed by steam distillation. The ester layer is separated. 

Photolytic Reaction in Sunlight A mixture of olefin (0.01 mole), formamide (40 g), r-butyl alcohol (20 ml), and acetone (5 ml) is placed in a Pyrex Erlenmeyer flask, which is then flushed with nitrogen, stoppered, and situated in direct sunlight for 1 day. A solution of olefin (0.04 mole), /-butyl alcohol (25 ml), and acetone (5 ml) is then added in four equal portions at 1-day intervals, and finally, the flask is left in sunlight for an additional 2 days. Work-up of the solutions as in the above procedure gives the desired amide in comparable yields. 

The authors actually detected the dibromomethylpropane and the r-butyl alcohol, but found no evidence for a-bromosulphides in their reaction products, which can be rationalized by the pathway outlined in equation (13). 

Studies of dimensiosolvatic effects have continued with an attempt to quantify them for solvolyses of 2-bromoadamantane in water-alcohol mixtures. Product selectivities S = fc(ether)/fc(alcohol) were measured at various concentrations of water in an alcohol and at various temperatures. The reciprocals of the averages of S values for 1.0 0.8 alcohol-water mixtures at all the experimental temperatures (120-150 °C) were proposed as measures D of dimensiosolvatic effects when a solvent molecule intervenes into contact ion pair to form solvent-separated ion pair. The scale runs from Z) = 1.0 (by definition) to D = 10.0 for r-butyl alcohol and is essentially a measure of the bulkiness of solvent molecules. 

Synonyms AI3-01288 Arconol BRN 0906698 r-BuOH f-Butanol tert-Butanol r-Butyl alcohol -Butyl hydroxide Caswell No. 124A CCRIS 4755 1,1-Dimethylethanol EINECS 200-899-7 2-Methyl-2-propanol 2-Methyl-/ propan-2-ol NCI-C55367 TBA Trimethyl carbinol Trimethylmethanol UN 1120. 

Lindamood C, Farnell DR, Giles HD, et al Subchronic toxicity studies of r-butyl alcohol in rats and mice. Fundam Appl Toxicol 19 91-100, 1992... 

In 1977 the U.S. EPA began allowing the use of r-butyl alcohol up to 7%. More recently 50 50 mixtures of /-butyl alcohol and methyl alcohol are being used, and ethyl alcohol has also become popular. When 10% ethyl alcohol is mixed with gasoline it is called gasohol and it is popular in states with good com crops, since the alcohol can be made from com fermentation. 

Samarium(ll) diiodide transforms aliphatic 1,5- and 1,6-dialdehydes (or keto aldehydes) into diols in the presence of an alcohol such as methanol or r-butyl alcohol (Equation (41)). The stereochemistry of the newly formed diols is usually -configuration. 448... 

As the name suggests, plastic crystals are generally soft, frequently flowing under their own weight. The pressure required to produce flow of a plastic crystal, as for instance to extrude through a small hole, is considerably less (2-14 times) than that required to extrude a regular crystal of the same substance. r-Butyl alcohol, pivalic acid and d-camphorprovide common laboratory examples of plastic crystals. The subject of plastic crystals has been reviewed fairly extensively (Aston, 1963 Sherwood, 1979) and we shall restrict our discussion to the nature of the orientational motion (Rao, 19856). 

Problem 13.50 Suggest a possible industrial preparation for (a) r-butyl alcohol, (f>) allyl alcohol, (c) glycerol (HOCHjCHOHCHjOH). ... 

The A-ring of the 17-ol (25) derived from equilenin 3-methyl ether is reduced rapidly under Birch reduction conditions, since the 1,4-positions are unsubstituted. The B-ring is reduced at a much slower rate, as is characteristic of aromatic compounds in which 1,4-reduction can occur only if a proton enters an alkylated position. Treatment of (25) with sodium and r-butyl alcohol in ammonia reduces only the A-ring to afford the corresponding 1,4-dihydro compound in over 85 % yield.40 On the other hand,... 

Irradiation of several members of the cannabinoid family has provided useful routes to some derivatives. Cannabichromene (576) is converted into cannabicyclol (577) when it is irradiated in r-butyl alcohol-acetone <71JCS(C)796) and tetrahydrocannabinolic acid (578) is aromatized to cannabinolic acid (579) (70CPB1327). 

A solution of cholestane-5a,6a-diol 6-tosylate (115a, 0.56 g)56,52 in dry r-butyl alcohol (20 ml) containing potassium f-butoxide (prepared from 40 mg of potassium) is allowed to stand at 25° for 15 min. The reaction mixture is diluted with water and extracted with ether. The ether extracts are washed with water and saturated salt solution, dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue (ca. 0.37 g) is crystallized from methanol to give 10(5 - 6)abeo-cholestan-5-one (116a, ca. 0.32 g) mp 125-126°. 

Common Name n-Butyl alcohol isobntyl alcohol scr-Butyl alcohol r-Butyl alcohol... 

A comparison of the suitability of solvents for use in Srn 1 reactions was made in benzenoid systems46 and in heteroaromatic systems.47 The marked dependence of solvent effect on the nature of the aromatic substrate, the nucleophile, its counterion and the temperature at which the reaction is carried out, however, often make comparisons difficult. Bunnett and coworkers46 chose to study the reaction of iodoben-zene with potassium diethyl phosphite, sodium benzenethiolate, the potassium enolate of acetone, and lithium r-butylamide. From extensive data based on the reactions with K+ (EtO)2PO (an extremely reactive nucleophile in Srn 1 reactions and a relatively weak base) the solvents of choice (based on yields of diethyl phenylphosphonate, given in parentheses) were found to be liquid ammonia (96%), acetonitrile (94%), r-butyl alcohol (74%), DMSO (68%), DMF (63%), DME (56%) and DMA (53%). The powerful dipolar aprotic solvents HMPA (4%), sulfolane (20%) and NMP (10%) were found not to be suitable. A similar but more discriminating trend was found in reactions of iodobenzene with the other nucleophilic salts listed above.46 Nearly comparable suitability of liquid ammonia and DMSO have been found with other substrate/nucleophile combinations. For example, the reaction of p-iodotoluene with Ph2P (equation (14) gives 89% and 78% isolated yields (of the corresponding phosphine oxide) in liquid ammonia and DMSO respectively.4 ... 

Osmium-catalysed dihydroxylation has been reviewed with emphasis on the use of new reoxidants and recycling of the catalysts.44 Various aspects of asymmetric dihydroxylation of alkenes by osmium complexes, including the mechanism, acceleration by chiral ligands 45 and development of novel asymmetric dihydroxylation processes,46 has been reviewed. Two reviews on the recent developments in osmium-catalysed asymmetric aminohydroxylation of alkenes have appeared. Factors responsible for chemo-, enantio- and regio-selectivities have been discussed.47,48 Osmium tetraoxide oxidizes unactivated alkanes in aqueous base. Isobutane is oxidized to r-butyl alcohol, cyclohexane to a mixture of adipate and succinate, toluene to benzoate, and both ethane and propane to acetate in low yields. The data are consistent with a concerted 3 + 2 mechanism, analogous to that proposed for alkane oxidation by Ru04, and for alkene oxidations by 0s04.49... 

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