Benzyl alcohol 3-methoxy

In some instances, treatment of polyfunctional benzylic alcohols with acid in the presence of organosilicon hydrides causes multiple functional group transformations to occur simultaneously. This phenomenon is illustrated by the reduction of the secondary benzylic alcohol function and concomitant loss of the methoxymethyl protecting group of 2-(l-hydroxydecyl)-5-methoxy-l-(methoxy-methyleneoxy)naphthalene upon treatment with Et3SiH/TFA in dichloromethane (Eq. 26).167... 

Decyl-5-methoxy-l-naphthol [Reduction of a Secondary Benzylic Alcohol to a Methylene Group with Concomitant Loss of a MOM Protecting Group].167... 

Decy 1-5-methoxy-1 -naphthol reduction procedure, benzyl alcohol reduction, 121... 

Certain classes of compounds are too reactive for the present method. Ethyl mandelate produced a racemic, protected phenyl glycine derivative. Benzylic alcohols with two methoxy groups (directly conjugating in the 2 and 4 positions) gave azide of 50% e.e. 

During the reaction of p-methoxy benzyl alcohol with silyl enol ether 31b, dibenzyl ether 33 was observed as a by-product, which disappeared after prolonged reaction time. In fact, if 33 was used as alkylating reagent, the silyl enol ether 31b was benzylated and the desired cyclopentanone 32e was obtained in a similar yield (Scheme 25). 

The addition of anilines to styrene oxide was reported to also proceed in the presence of 10mol% 37 affording the corresponding P-amino alcohols 1-5 in yields ranging from 75% to 92% (Scheme 6.37). Additionally, urea derivative 37 (20mol% loading) was found to catalyze the addition of aniline (2.0 equiv.) to ( )-stilbene oxide (92% yield 5.9 d 30°C), the addition of thiophenol (2.0 equiv.) to 2-methoxy styrene oxide (85% 20h rt), and the alcoholysis of 4-methoxy styrene oxide with benzyl alcohol (2.0 equiv.) affording the respective P-alkoxy alcohol (82% 20h rt). 

Methoxy-2,2,6,6-tetramethyl-1 -oxopiperidinium chloride, 183 Osmium tetroxide, 222 Samarium(II) iodide, 270 Reagents suitable for oxidation of benzyl alcohols but not other primary alcohols... 

Ref 46a Two benzylic alcohols are selectively oxidized with active M11O2 in the presence of two secondary amines. In a similar compound, possessing two methoxy substituents in the place of the two fluorine atoms, the corresponding oxidation provides a modest 34% yield of the desired dialdehyde. This happens because the methoxy substituents render the amines more oxidation-sensitive. ... 

Alcohols 1-butanol, 1-pentanol, 1-hexanol, 2-ethyl-l-hexanol, 1-heptanol, 1-octanol, 1- decanol, l-methoxy-2-propanol, butoxyethanol, ethoxyethanol, 2- (2-butoxyethoxy) ethanol, benzyl alcohol, 1-dodecanol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-octadecanol... 

The reactions of 4/3- acetoxythaliporphine (48) with nucleophiles have been studied. On dissolution in methanol, the 4-methoxy-analogue (49) is obtained, but the bulkier alcohols ethanol and benzyl alcohol require the presence of boron trifluoride etherate to generate the ethers (50) and (51). Loss of stereospecificity at C-4 was observed when isopropyl alcohol and cyclohexanol were the nucleophiles.33... 

The parallelism in reactions with HMPT and mixtures of phosphorus pentoxide and amines can best be realized by looking at the mechanism of HMPT reactions [1 5 ]. In the reaction of p-methoxy-benzylalcohol with HMPT which produce the corresponding N,N-dimethylbenzyl amine--p-methoxybenzyl phosphate was identified in the XP NMR spectrum of the reaction mixture. Since pyrophosphate was also observed during the reaction of the benzyl alcohol with HMPT, the intermediate formation of the metaphosphate anion can be assumed. Addition of the benzyl alcohol to that anion then produce the benzyl phosphate. Phosphate ions are known to be good leaving groups so that a benzylamine can easily be produced from the phosphate by reaction with di-methylamine released from the dimethylammonium ion. The phosphoric acid produced during the reaction is believed to react with HMPT, so that more dihydro-gen-bis(dimethylammonium) pyrophosphate is formed. 

Redox potential is a catalytically relevant property of heme peroxidases, as in theory, sets the limit for the oxidative ability of the enzyme. An inverse correlation was found between the activity and the redox potential of methoxybenzenes and methoxy-substituted benzyl alcohols for lignin peroxidase (LiP) and horseradish peroxidase (HRP) [42, 43]. These enzymes were able to catalyze the oxidation of methoxybenzenes with redox potential as high as 1.45 V and 1.12 V, respectively [42]. In the case of methoxy-substituted benzyl alcohols, the maximum substrate redox potential was 1.39 V for both enzymes [43]. This type of correlation has allowed ranking enzymes from the more oxidant to the less oxidant. The inverse... 

Hong F, Jonsson LJ, Lundquist K et al (2006) Oxidation capacity of laccases and peroxidases as reflected in experiments with methoxy-substituted benzyl alcohols. Appl Biochem Biotechnol 129-132 303-319... 

Dichloro 5 bromo 2 methoxy benzyl alcohol dicamba... 

On the other hand, if the methoxy group is in the meta position, the benzyl alcohol reacts at only about one-third the rate at which benzyl alcohol itself reacts. The tn-methoxybenzyl carbonium ion is not stabilized by resonance forms analogous to those of the para compound. The ease of attaining the carbonium ion is thus greatly diminished, and if the ion is formed in the transition state, the energy of activation should be greater in the meta compound than it is in the para compound. The order of reactivity of the various substituted benzyl alcohols is... 

This effect of the p-methoxy group in promoting the homologation reaction is consistent with its similar effect in the benzyl alcohol series. The isolation of the alcohol is also additional evidence for the intermediate formation of a carbinol in the reduction of an aromatic ketone to the hydrocarbon. 

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