O-Methoxybenzyl alcohol

Problem 19.21 Use phenol and any aliphatic and inorganic compounds to prepare (a) o-chloromethylphenol, (b) o-methoxybenzyl alcohol, (c) p-hydroxybenzaldehyde. 

O-Methoxybenzyl alcohol (2) and o-Methyloxybenzolc acid (3)3 To a solution ot KOH (120 g, 2 mol) in water are added o methyoxybenzaldehyde 1 (136 g, 1 mol) under efficient stlmng and external cooling with water Stirring was mamtained until a stable emulsion was obtained After 24 h at 30°C, the mixture was diluted with water and extracted with Et20 Evaporation of the solvent and vacuum distillation of the residue afforded 55 g of 2 (79%), bp 245-255°C Acidification ot the aqueous solution, extraction with EI2O and distillation of the solvent gave 3, mp 98 100°C... 

CAS 612-16-8 EINECS/ELINCS 210-296-5 Synonyms Benzenemethanol, 2-methoxy- 2-Methoxybenzenemethanol 2-Methoxybenzyl alcohol o-Methoxybenzyl alcohol... 

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). 

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... 

Reduction ofp-methoxybenzaldehyde, typical procedure method A To lithium phenyltel-lurolate prepared from PhLi (2.1 M, 4 8 mL, 10 mmol) and Te (1.27 g, 10 mmol) in THF (30 mL) under Nj is added p-methoxybenzaldehyde (0.272 g, 2 mmol) at -78°C followed by TFA (0.77 mL, 10 mmol). The solution is stirred for a further 2 h, and allowed to warm at room temperature. H O (200 mL) is added and the product is extracted with ether. The extract is dried (Na2S04), evaporated and the residue separated by SiOj chromatography from the formed diphenyl ditellnride, giving p-methoxybenzyl alcohol (0.23 g (93%)). 

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. 

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). 

The overhydrogenation of aromatic aldehydes beyond benzylic alcohols is rarely important with copper-chromium oxide and Raney nickel unless the reaction conditions are too vigorous. Thus, over copper-chromium oxide o- and p-methoxybenzaldehydes were hydrogenated to the corresponding methoxybenzyl alcohols in high yields in methanol at 110-125°C and 22-24 MPa H2 (eq. 5.18).42 At 185°C, however, / -methoxybenzyl alcohol was hydrogenolyzed to give p-cre-sol methyl ether (eq. 5.18). 

A total of 0.33 g (1.68 mmol) of 4-allyloxy-3-methoxybenzyl alcohol (1) and 0.32 g (1.69 mmol) of p-toluenesul Ionic acid monohydrate were ground together to produce a sticky, pale brown syrup which solidified over a period of 2 days to yield tris-(O-allyl) cyclotriveratrylene. The solid material was dissolved in di-chloromethane, insoluble materials were removed by filtration, and the pure crystalline product was obtained by slow evaporation of the solvent. The white crystalline product (0.16 g, 54%) obtained proved to be pure tris-(C)-allyl) cyclotriveratrylene (2) when compared with authentic samples by melting point, TLC, and XH NMR analysis. 

Two methods for the photolytic generation of />-methoxybenzyl radicals, by C-H cleavage in /7-methoxytoluene and C-O cleavage in p-methoxybenzyl alcohol, have been studio in n-heptane solution by nanosecond fluorescence and absorp-... 

Methoxybenzyl acetate p-M ethoxy benzyl acetate. See p-Anisyl acetate 4-Methoxybenzylacetone. See 4-p-Methoxyphenyl-2-butanone 2-Methoxybenzyl alcohol. See o-Anisyl alcohol 4-Methoxybenzyl alcohol. See p-Anisyl alcohol 4-Methoxybenzyl alcohol (o-, m-, p-). See Anisyl alcohol... 

Methoxybenzyl alcohol. See o-Anisyl alcohol p-Methoxybenzyl alcohol. See p-Anisyl alcohol p-Methoxybenzyl butyrate. See Anisyl butyrate 4-Methoxybenzyl formate p-Methoxybenzyl... 

A number of groups have used CB[n] photoreactors to catalyze the oxidation of guest molecules [152-154]. Cong and coworkers [152] showed that dehydration of veratry alcohol 47 to veratryaldehyde 48 by the oxidizing agent o-iodoxybenzoic acid 49 (Fig. 3.22) was enhanced by the presence of CB[8], both in terms of reaction time and in terms of % conversion. The same trends were observed for other benzyUc alcohols as well, including benzyl alcohol and 3-methoxybenzyl alcohol. Furthermore, CB[8] was shown to provide... 

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