2-Methoxybenzyl alcohol

Among the experiments that have been cited for the viewpoint that borderline behavior results from simultaneous SnI and Sn2 mechanisms is the behavior of 4-methoxybenzyl chloride in 70% aqueous acetone. In this solvent, hydrolysis (i.e., conversion to 4-methoxybenzyl alcohol) occurs by an SnI mechanism. When azide ions are added, the alcohol is still a product, but now 4-methoxybenzyl azide is another product. Addition of azide ions increases the rate of ionization (by the salt effect) but decreases the rate of hydrolysis. If more carbocations are produced but fewer go to the alcohol, then some azide must he formed by reaction with carbocations—an SnI process. However, the rate of ionization is always less than the total rate of reaction, so some azide must also form by an Sn2 mechanism. Thus, the conclusion is that SnI and Sn2 mechanisms operate simultaneously. ... 

The incubation of 3,5-dichloro-4-methoxybenzyl alcohol with methanogenic sludge produced the de-O-methylated compound that was transformed to 2,6-dichlorophenol, and abiotically dimerized to fciX3,5-dichloro-4-hydroxyphenyl)methane (Verhagen et al. 1998) (Figure 2.2e). 

FIGURE 2.2 Transformation of (a) 5-aminonaphthalene-2-sulfonate, (b) benzo[fc]thiophene, (c) 4-chloro-biphenyl, (d) 4-nitrotoluene, (e) 3,5-dichlor-4-methoxybenzyl alcohol, (f) 2,3-diaminonaphthalene in presence of nitrate, and (g) 3,4-dichloroaniline presence of nitrate. 

Palmisano, G., Yurdakal, S., Augugliaro, V., Loddo, V., and Palmisano,L. (2007) Photocatalytic selective oxidation of 4-methoxybenzyl alcohol to aldehyde in aqueous suspension of home-prepared... 

Quite recently, the structure of pelagiomicins B (60) and C (61) was confirmed by a synthesis starting from griseoluteic acid (62) [60]. In the first synthesis of 62, Holliman et al. employed the reductive cyclization of o-nitrodi-phenylamines using NaBH4 to yield phenazines [84]. To this end, 3-amino-4-methoxybenzyl alcohol (99) was treated with methyl 2-bromo-3-nitrobenzoate (100) to yield the o-nitrodiphenylamine 101, which by reductive cyclization... 

For the recyclability of catalyst 1, after completion of the oxidation of 4-methoxybenzyl alcohol, the reaction mixmre was treated with water (3 mL), and the organic layer, after drying (Na2S04) and GC analysis, was passed through a short pad of silica gel using ethyl acetate and hexane as eluent to afford analytically pure 4-methoxybenzaldehyde in quantitative yield. Evaporation of the aqueous layer afforded the copper complex 1 that was subsequently reused for the oxidation of 4-methoxybenzyl alcohol up to three times using fresh TEMPO whereupon no loss of activity was observed. 

Baciocchi et al43 have reported the existence of the pH-dependent mechanistic dichotomy for the deprotonation of 4-methoxybenzyl alcohol radical cation in aqueous solution. In neutral and acidic solutions the 4-MeOC6H4CH2OH + radical cation undergoes C-H deprotonation, while in basic solution (pH 10), the reaction is initiated by deprotonation of the OH group. DFT calculations were carried out and reveal that the OH induced O-H deprotonation is consistent with the charge controlled reaction, while the C-H deprotonation, observed when the base is HjO, appears to be effected by frontier orbital interactions43. 

A mixture of 4-methoxybenzyl alcohol le (5 mmol) and acetic anhydride (5 mmol) in a beaker covered with watch glass was irradiated by microwaves for 10 min (heating and cooling at the interval of 1 min). After completion of die reaction (TLC), the product was extracted with ether (3x15 mL). The ether layer was washed with 10% NaOH and then dried with anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave 4-methoxybenzyl acetate 2e in excellent yield (95%). 

The mechanism of base-catalysed deprotonation of the a-CH of 4-methoxybenzyl alcohol radical cations in water has been examined. There is no direct attack of HO- at the a-CH as was believed, but reaction occurs via deprotonation of the OH to produce the benzyloxy radical, which then forms the carbon-centred radical by a 1,2-hydrogen... 

Benzyl-l,2,3-triazole 1-oxides are prone to undergo ring opening when treated with strong bases. Thus 2-(4-methoxybenzyl)-l,2/3-triazole 1-oxide 445 upon treatment with LDA at -78°C in the absence of electrophiles gives rise to 4-methoxybenzyl alcohol 447 as the solely isolable product. A putative mechanism for this transformation is shown in Scheme 128. 

A similar dyad was described by Cibulka et al. [20] The flavin part was in this case covalently bound to the zinc(II)-cyclene. 4-Methoxybenzyl alcohol was bound to the metal centre and was upon irradiation oxidised to the corresponding benzaldehyde (Scheme 23). 

Cibulka, R., Vasold, R., Konig, B. Catalytic photooxidation of 4-methoxybenzyl alcohol with a flavin... 

Substituted o-benzenesulfonamide 61 was found to be a good source for the synthesis of 4-methoxybenzyl esters by the reaction with alcohols and phenols in the presence of sodium hydride at room temperature <1998TL1799>. Treatment of cyclic sulfonamide 61 with aqueous KOH in dimethylformamide (DMF) yielded 4-methoxybenzyl alcohol together with benzenesulfonamide 53 (Scheme 5). 

Partial oxidation 2-propanol 4-methoxybenzyl alcohol Cyclohexane Hydrocarbons... 

Synthesis of 4-Methoxybenzaldehyde (8) by Aerobic Oxidation of 4-Methoxybenzyl Alcohol, Catalyzed by 6 [4]... 

A solution of 92.6 mmol (12.8 g) 4-methoxybenzyl alcohol, 2.25 mmol nitroxyl radical 6, 4.5 mmol p-toluensulfonic acid, 1.8 mmol Mn(N03)2, and 1.8 mmol Cu(N03)2 in 100 mL CH3COOH was stirred at r.t. for 3h under air at atmospheric pressure. The CH3COOH was then evaporated at ca. 55 torr and the reaction product was extracted with methyl-t-butyl ether (the salt of the nitroxyl radical 6 with p-toluensulfonic acid, can be recovered and recycled). GC analysis (4-methylbenz-... 

Methoxybenzyl alcohol 38, 50 g, 362 mmol (Avocado 15559, Acros 15973, Lancaster 2566, Aldrich 13,690-5, Fluka 64840)... 

Meunier has developed model chemistry for peroxidases such as ligninase with KHSO5 as oxo-transfer oxidant and Fe or Mn-tetrasulfoporphyrin in aq. MeCN. These catalysts oxidize lignin models such as veratryl alcohol (3,4-methoxybenzyl alcohol) to give biologically relevant products such as quinones. 

SYNS ANISE ALCOHOL ANISIC ALCOHOL p-ANISOL ALCOHOL ANISYL ALCOHOL (FCC) FE.MA No. 2099 4-METHOXYBENZENEMETHANOL 4-METHOXYBENZYL ALCOHOL... 

The 4-methoxybenzyl esters are prepared by transesterification of N-protected amino acid nitrophenyl esters with 4-methoxybenzyl alcohol in the presence of several equivalents of imidazole, followed by subsequent acidolytic cleavage of the N-protecting group.Alternatively, reaction of N-protected amino acids silver(I) salts with 4-methoxybenzyl halides (TEA/CHCI3, rt, 24 h, 60% yield) or treatment of N-protected amino acids with 4-meth-... 

As a general rule, oxygen substituents are lost from benzylic positions during metal-ammonia reductions. An important set of exceptions are those compounds which possess a methoxy group in a para relationship to the benzylic substituent. Thus, 4-methoxybenzyl alcohol (208) may be reduced in high yield... 

Reduction of l-(4-methylphenyl)ethanol affords a 4 1 mixture of the 2, 5 -dihydro derivative with 4-ethyltoluene," showing again the influence of an electron-releasing substituent in the para position. The result with 4-methoxybenzyl alcohol appears to be completely general. Benzylic hydroxy groups may also be preserved when the proximal aryl ring is hydroxylated, as in the formation of (207 Scheme 42) and in the reduction outlined in Scheme 45." ... 

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