Compounds alkylation with alcohol

Alkylation of benzene using alpha olefins produces linear alkylbenzenes, which are further sulfonated and neutralized to linear alkylbenzene sulfonates (LABS). These compounds constitute, with alcohol ethoxy-sulfates and ethoxylates, the basic active ingredients for household detergents. Production of LABS is discussed in Chapter 10. 

Generally the best result.s are obtained when the alcoholate of a fluorinated compound reacts with a nonfluorinated alkyl halide. Yields decrease when both alcohol and halide contain fluorine. The reaction of dichloro compound 9 with alcoholates 10 to monoethers II is representative of a variety of similar transformations (which proceed via an addition/elimination mechanism) of cyclopropcne, cyclobutene.cyclopentene" or cyclohexene derivatives." ... 

Alkylation with a vatiety of common alkyl halides oi sulfates gives stable dialkylcyanamides. However, the intermediate monoalkylated compounds usually cannot be isolated and cychc trimers or cotrimers with cyanamide ate obtained (13). The reaction can be carried out efficientiy in water or alcohol. Allyl chloride is an especially useful reagent, producing diallylcyanamide [538-08-9J (4). 

Ketones and alcohols are frequently used as alkylating agents Ketones often condense with two molecules of an aromatic compound through an alcohol intermediate [79, 20, 21] T,r,I -Trifluoroacetophenone and aniline afford 1,1 bis(4-ammophenyl) 1 phenyl 2,2,2-trifluoroethane [27] (equation 14)... 

When the additional nitrogen atom is included in one of the aromatic rings, on the other hand, there is obtained a compound with antihistaminic properties. Reaction of the Grignard reagent from 4-chlorobromobenzene with pyridine-2-aldehyde gives the benzhydrol analog (12). The alcohol is then converted to its sodium salt by means of sodium, and this salt is alkylated with W-C2-chloroethyl)dimethylamine. Carbinoxamine (13) is thus obtained. ... 

In an alternate approach to the preparation of compounds containing the additional ring, haloamide, 41 (obtained from the aminobenzophenone and bromoacetylbromide) is alkylated with etha-nolamine to afford 42. Treatment of the amino alcohol in acetic acid affords the carbonyl addition product, 43, at the same time... 

In an attempt to study the behavior and chemistry of coal in ionic liquids, 1,2-diphenylethane was chosen as a model compound and its reaction in acidic pyri-dinium chloroaluminate(III) melts ([PyHjCl/AlCb was investigated [69]. At 40 °C, 1,2-diphenylethane undergoes a series of alkylation and dealkylation reactions to give a mixture of products. Some of the products are shown in Scheme 5.1-40. Newman also investigated the reactions of 1,2-diphenylethane with acylating agents such as acetyl chloride or acetic anhydride in the pyridinium ionic liquid [70] and with alcohols such as isopropanol [71]. 

The Friedel-Crafts allcylation reaction usually involves the interaction of an allcy-lation agent such as an alkyl halide, alcohol, or alkene with an aromatic compound, to form an alkylated aromatic compound (Scheme 5.1-44). 

Alkylation of alcohols or phenols with diazo compounds... 

Organophosphate Ester Hydraulic Fluids. Organophosphate esters are made by condensing an alcohol (aryl or alkyl) with phosphorus oxychloride in the presence of a metal catalyst (Muir 1984) to produce trialkyl, tri(alkyl/aryl), or triaryl phosphates. For the aryl phosphates, phenol or mixtures of alkylated phenols (e.g., isobutylated phenol, a mixture of several /-butylphenols) are used as the starting alcohols to produce potentially very complex mixtures of organophosphate esters. Some phosphate esters (e.g., tricresyl and trixylyl phosphates) are made from phenolic mixtures such as cresylic acid, which is a complex mixture of many phenolic compounds. The composition of these phenols varies with the source of the cresylic acid, as does the resultant phosphate ester. The phosphate esters manufactured from alkylated phenylated phenols are expected to have less batch-to-batch variations than the cresylic acid derived phosphate esters. The differences in physical properties between different manufacturers of the same phosphate ester are expected to be larger than batch-to-batch variations within one manufacturer. 

Metal alkoxides undergo alkoxide exchange with alcoholic compounds such as alcohols, hydro-xamic acids, and alkyl hydroperoxides. Alkyl hydroperoxides themselves do not epoxidize olefins. However, hydroperoxides coordinated to a metal ion are activated by coordination of the distal oxygen (O2) and undergo epoxidation (Scheme 1). When the olefin is an allylic alcohol, both hydroperoxide and olefin are coordinated to the metal ion and the epoxidation occurs swiftly in an intramolecular manner.22 Thus, the epoxidation of an allylic alcohol proceeds selectively in the presence of an isolated olefin.23,24 In this metal-mediated epoxidation of allylic alcohols, some alkoxide(s) (—OR) do not participate in the epoxidation. Therefore, if such bystander alkoxide(s) are replaced with optically active ones, the epoxidation is expected to be enantioselective. Indeed, Yamada et al.25 and Sharp less et al.26 independently reported the epoxidation of allylic alcohols using Mo02(acac)2 modified with V-methyl-ephedrine and VO (acac)2 modified with an optically active hydroxamic acid as the catalyst, respectively, albeit with modest enantioselectivity. 

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