Benzyl alcohol, reactions with

N-Benzylacetamide, 43,18 n-Benzylacrylauide, 42,16 Benzyl alcohol, reaction with acrylonitrile, 42, 16... 

Benzophenone, conversion to ethyl /S-hydroxy-0,0-diphenylpro-pionate, 44, 57 Benzophenone oxime, 44, 52 Benzopyrazole, 42, 69 3-Benzoylpropionic add, condensation with benzaldehyde to give a-benzylidene-y-phenyl-A y -bu-tenolide, 43, 3 N-Benzylacetamide, 42,18 n-Benzyiacrylamide, 42,16 Benzyl alcohol, reaction with acrylonitrile, 42,16... 

Dehydration reactions catalysed by NHC complexes have been reported where a new C-C bond is formed. Peris has used [Ir(OTf)2Cp (NHC)] complexes including compound 35 to benzylate arenes with alcohols and other reagents [14]. For example, the dehydrative C-C coupling of benzyl alcohol 8 with toluene 33 is catalysed by 0.1 mol% of 35 to give a mixture of benzylated products 34 (Scheme 11.8). 

Benzyl alcohol contaminated with 1.4% of hydrogen bromide and 1.1% of dissolved iron(II) polymerises exothermally above 100°C. Bases inhibit the polymerisation reaction. In a laboratory test, alcohol containing 1% of HBr and 0.04% of Fe polymerised at about 150° with an exotherm to 240° C. Formation and iron-catalysed poly-condensation of benzyl bromide seems to have been implicated. See Benzyl bromide Molecular sieve, or Catalytic impurities See Other BENZYL COMPOUNDS, POLYCONDENSATION REACTION INCIDENTS... 

The cooled reaction product is treated with 200 cc. of water, the layer of oil separated, washed once with a second portion of water, and subjected to distillation in vacuo. The first fraction of the distillate contains benzyl alcohol together with unchanged aldehyde, as well as a small quantity of water. The temperature then rises rapidly to the boiling-point of benzyl benzoate, when the receivers are changed. The product boils at 184-185°/15 mm., and analysis by saponification shows it to consist of 99 per cent ester. A yield of 410-420 g. is obtained, which corresponds to 90-93 per cent of the theoretical amount. This benzyl benzoate supercools readily, but after solidifying... 

Butyl alcohol and benzene gave both mono- and di-i-butylbenzene (Simons et al., 37). Allyl alcohol reacted with benzene to produce both allylbenzene and 1,2-diphenylpropane. (Simons and Archer, 38.) The activity of the hydroxyl group is indicated in the fact that 2-phenyl-propanol was not separated. Benzyl alcohol reacted with benzene to form diphenylmethane (Simons and Archer, 39) despite the fact that this reaction is reported (Calcott et al., 34) to form 1,2,3,4,5,6-hexa-phenylcyclohexane by the polymerization of the alcohol. Isopropyl alcohol with benzene gave isopropylbenzene, 1,4-diisopropylbenzene,... 

Hydrogenation of benzaldehyde yields benzyl alcohol, condensation with aliphatic aldehydes leads to additional fragrance substances or their unsaturated intermediates. Unsaturated araliphatic acids are obtained through the Perkin reaction, for example, the reaction with acetic anhydride to give cinnamic acid. 

However, these cations are stabilized by an arenechromium tricarbonyl group in the a-position. Thus benzyl alcohol complexed with chromium tricarbonyl undergoes Ritter reactions rapidly and in high yield (equation I). On the other hand, the... 

The reactivities of alkyl halides are in the sequence RI > RBr > RCl and MeX > EtX > PrX. Benzyl hahde reactions with tin do not require catalysts (equation 2). For less reactive halides, the catalysts and promoters employed include metals (sodium, magnesium, zinc, or copper), Lewis bases (amines, triorganophosphines and -stibines, alcohols, or ethers), iodides, and onium salts (R4MX). The use of tin-sodimn alloys can result in tri- or tetraorganotin products. Electrochemical synthesis has also been reported, e.g. the formation of R2SnX2 from the oxidation of anodic tin by RX in benzene solution and the formation of ILtSn from RI (R = Me or NCCH2CH2) and cathodic tin. 

Titanium acetylides react with 3-benzyl-tetrahydro-l,3-oxazines and 1,3-oxazolidines to give the corresponding / -aminoacetylenes in modest to good yield.296 Vinyl Ti(iv) species prepared by the alkylation of vinylcarbene complexes with BTCl react with aldehydes to give allylic alcohols. Reaction with terminal alkynes produces conjugated dienes, in which a vinyl group regioselectively bonds to the unsubstituted side of carbon-carbon triple bond.297... 

FIGURE 8. Two likely types of redox reaction of marine humus showing oxidation of a cyclohexene (top) and a benzylic alcohol (bottom) with concomitant transfer of the electrons to a metal, M. 

State. The pre-steady-state changes are consistent with the rapid oxidation of bound alcohol, the concomitant formation of bound NADH, and the perturbation of LMCT bands from the Co(II) center. In the 450 to 700 nm region (Fig. 8A), the time-resolved spectra show that a transient species with a Xmax of 570 nm is formed very rapidly and decays with a rate that is similar to the rate of appearance of enzyme-bound NADH (compare the insets to Figs. 7Aa and 8Aa). It is notable that the d d transitions of the species formed in the very fast initial phase of the benzyl alcohol reaction are highly similar both to those of the stable CoIIHEINAD", trifluoroethanol) complex (Fig. 9) and to the transient species seen in the reduction of benzaldehyde. Below pH 7.5, the amount of intermediate that accumulates decreases. Traces of the intermediate are detectable in the spectra collected at pH 5.6 (Fig. 8C). At pH 4.8, this species could not be detected (Fig. 8B,D). At that pH, the spectral changes indicate... 

Dynamic Kinetic Resolution. Another typical acid-catalysed reaction is the racemisation of chiral alcohols, due to inversion at the chiral carbon. This can actually be made use of in the formation of enantiopure compounds, by dynamic kinetic resolution using an enzyme, such as a lipase, that catalyses enantioseleetive esterification in an organic medium. By coupling zeolite Beta-catalysed intereonversion of benzylic alcohol enantiomers with enzyme-catalysed esterifieation of only one of the enantiomeric alcohols, almost complete eon version to enantiopure ester ean be achieved. ... 

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