The Preparation and the Antibacterial and Antifungal Properties of Some Substituted Benzyl Alcohols

Abstract

A number of substituted benzyl alcohols have been prepared and together with some related, commercially available, compounds have been tested for antibacterial and antifungal properties. The most active inhibitory compound was 3:4:5‐trichlorobenzyl alcohol followed by 4‐chloro‐3:5‐dimethyl‐, 3:4‐dichloro‐ and 2:4‐dichlorobenzyl alcohols, but saturated aqueus solutions of the last three compounds were more rapidly bactericidal. Pharmacological tests have shown that 2:4‐dichlorobenzyl alcohol has low toxicity.

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

“…[54] Benzyl methyl ethers were almost exclusively prepared by the classical Williamson synthesis, by treatment of an MeOH solution of the appropriate halide (100.0 mmol in 100 mL) with MeONa in MeOH (200 mmol in 100 mL), by a described procedure (Method A). [55] 1-(Methoxymethyl)-3-methylbenzene (1c, 11.02 g, 81% from the chloride), [56] 1-(1,1-dimethylethyl)-4-(methoxymethyl)benzene (1e, 14.60 g, 82% from the bromide), [57] 1-chloro-2-(methoxymethyl)benzene (1f, 11.70 g, 75% from the chloride), [58] 1-chloro-3-(methoxymethyl)benzene (1g, 12.48 g, 80% from the chloride), [58] 1-chloro-4-(methoxymethyl)benzene (1h, 12.17 g, 78% from the chloride), [59] 1,3-dichloro-4-(methoxymethyl)benzene (1j, 17.57 g, 92% from the chloride), [60] 1-(methoxymethyl)-2-nitrobenzene (1k, 12.53 g, 75% from the iodide), [61] 1-(methoxymethyl)-3-nitrobenzene (1m, 13.03 g, 78% from the iodide), [62] 1-(methoxymethyl)-4-nitrobenzene (1n, 12.69 g, 76% from the iodide), [62] and diphenylmethyl methyl ether (1hh, 17.62 g, 89% from the chloride) [63] were prepared by Method A. [(1,1-Dimethylethoxy)methyl]benzene [64] (1dd, 7.22 g, 44%) was prepared in a similar way, from benzyl bromide and potassium tert-butoxide.…”

Chemoenzymatic ortho-quinone methide formation

“…As a comparative measure, we subjected substrate 16 to several chemical oxidation conditions and did not observe conversion to desired benzylic alcohol 17 (see Supporting Information, Table S1). For example, attempts to oxidize 16 with DDQ 39 resulted in over-oxidation to the bisaldehdye and exposure of 16 to MnO2 40 or Ag2O 41 resulted in no observed reaction. Efforts to perform a benzylic hydroxylation with K2S2O8 42 or cerium ammonium nitrate 43 led to decomposition of the substrate.…”

Chemoenzymatic ortho-quinone methide formation

“…Phenol 39 was converted to the corresponding benzylic alcohol; however, the position of the hydroxyl group proved to be important for catalysis as phenol S5 was not oxidized by either CitB or ClaD. These results motivated us to synthesize an additional panel of phenolic substrates to further assess the scope of NHI biocatalytic hydroxylation (40)(41)(42). In the case of CitB, increasing the steric bulk at the C5 position increased the conversion of substrates to hydroxylated products except for 2-naphthyl substrate 42, which demonstrated decreased conversion, possibly reflecting the steric limitations of the CitB active site.…”