Potassium alcoholate

Etherification. A chemical reaction forming ethers, such as the reaction of sodium or potassium alcoholates (RONa) with an alkyl halide (R Cl) giving the ether ROR and NaCl. 

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Fio. 11.—Possible Structure of the Potassium Alcoholate of l,ft-Anhydro-/S-D-glucopyranose. 

The preparation of the potassium alcoholate requires much care. Metalation of the alcohol is carried out to completion without attack of the double bond by means of diphenylmethyl potassium in THF solution. Excess alcohol present in the subsequent polymerization system would act as a transfer agent. 

In this method mono- or dihydroxy-terminated polyoxyethylene oligomers are reacted in bulk with potassium metal at 120 °C, thus converting quantitatively the hydroxy groups into potassium alcoholate functions. Then, the medium is heated up to 180 °C and acetylene is added. This addition to the alcoholates quantitatively produces mono- or divinyl-terminated polyoxyethylenes, respectively ... 

It was Hepp [30] in 1882 who first found that sym-trinitrobenzene forms a dark coloured substance with sodium alcoholate. V. Meyer [38] isolated a similar substance in 1896 when treating sym-trinitrobenzene with potassium alcoholate, and assigned the following structure to it ... 

Angeli [39] suggested in 1884 that the addition of potassium alcoholate occurs through one of the nitro groups ... 

Hantzsch and Kissel [81] by treating trinitrotoluene with potassium alcoholate (e.g. methylate) obtained an addition product to which they ascribed the structure given earlier by Angeli [82] for the product obtained from trinitrobenzene and CH3OK (I). 

Stefanovich [88], on the basis of Meisenheimer s formulae, ascribes the formulae VII and VIII to the addition products of a- trinitrotoluene with two or three molecules of potassium alcoholate respectively. 

There is evidence that the reaction product of trinitrotoluene with potassium alcoholate, which explodes when heated to 130-150°C, may even ignite spontaneously at room temperature. 

By crystallization from methyl alcohol trinitrophenetole is converted into trinitroanisole. It also adds on a molecule of sodium or potassium alcoholate to form a bright coloured salt. 

In the wake of the successful use of Schlosser s base, a variety of superbasic reagents have been studied, showing sometimes a modulated behavior. It must be pointed out, however, that the simple substitution of one component with a similar reagent (e.g., potassium tert-butoxide with another potassium alcoholate) affects the overall behavior of the base only to a small extent. In contrast, the use of different organolithium components (butyl-, sec-butyl, tert-butyl, and methyllithium) is often responsible for marked differences in the reactivity profiles.40... 

Anionic graft-polymerization of paraformaldehyde onto starch and dextrin has been effected in methyl sulfoxide solution, polymerization being initiated by the carbohydrate potassium alcoholate formed from the reaction of the carbohydrate with naphthalene potassium, a metallation procedure not previously described for carbohydrates.220... 

MetalUuion ofl-dehydrocholesterol. Although 7-dehydrocholesterol has three different allylic positions, deprotonation of the potassium alcoholate 1 with this base followed by carboxylation and subsequent esterification results in the diastereomeric esters 2 as the major products. On equilibration of the mixture, the major isomer (probably the 3-isomer)... 

The Pinner reaction is the standard method of preparing imidate salts (the free imidate is obtained upon basification with weak bases) by alcoholysis of nitriles in the presence of mineral acids. However, this method is not suitable for the synthesis of allylic imidates since, under these reaction conditions, allylic amides, the product of the Ritter reaction, are formed. The acetimidates are easily prepared by condensation of the sodium or potassium alcoholate with trichloro- or trifluoroacetonitrile in high yield. For the rearrangement reaction the crude imidates can be used. 

Remark In complex bases, cations of the activated base and cations of the activating agent are identical. We never activated, for instance, a base having a sodium cation with potassium alcoholates. 

In anionic polymerization, B-propiolactone initiated with potassium alcoholate, gives,in initiation,both alco-holate and carboxylate anions. Alcoholate ions in every next step convert partially into carboxylate whereas carboxylate reproduce themselves quantitatively. Thus, after a few steps only carboxylate anions are left (14). Related situation was observed in the polymerization of styrene oxide (15). Here, however, it is only due to the structure of the initiator used. Thus, when in the initiation step both secondary and primary alcoholate anions are formed, due to the low steric requirements, in the next step apparently only the attack on the least substituted carbon atom takes place and already in the second step exclusively secondary alcoholate anions are present. 

Between KOH and the hydroxyl groups there is a well known equilibrium reaction, with the formation of a potassium alcoholate and water [2, 4, 9-14, 49, 50, 52-54, 56-61] ... 

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