M-Phenoxybenzyl alcohol

In 1958, Barthel et al. [25] reported dimethrin (15), which was the first substituted benzyl alcohol ester of chrysanthemic acid. This compound was not put into practical use due to its low insecticidal activities. Phenothrin (16), one of the m-phenoxybenzyl alcohol esters developed by Fujimoto et al. [26], was found to have superior chemical stability as well as safety, and has been the sole pyrethroid used as a lice control agent for humans. Further improvement was made by Matsuo et al. [27] who introduced a cyano function at the a position of the benzyl part of phenothrin, leading to a-cyano-m-phenoxybenzyl alcohol esters (17). Thereafter, this alcohol moiety has been used as a component for a number of photostable pyrethroids for agricultural purposes however, the development of cross-resistance can be seen in some pests. 

Electrosynthesis of m-phenoxybenzyl alcohol (16) successfully went through the pilot plant test in 1987 and started commercial production at the beginning of 1988. 

Studies with m-phenoxybenzyl alcohol in cotton leaves suggested that the B-O-glucoside of this xenobiotic undergoes rapid turn-over within the cell (30). 

The simultaneous determination of permethrin, A A -diethyl-m-toluamide, and pyridostigmine and their degradation compounds (m-toluamide, m-toluic acid, N-methyl-3-hydroxypyridinium bromide, m-phenoxybenzyl alcohol, m-phenoxyben-zoic acid) were extracted from urine and plasma and analyzed on a Cjg column (2 = 208-230 nm). A two-ramp 99/1 -> 25/75 (at 6 min) -> 1/99 (at 11 min hold 4min) water (to pH 3.2 with acetic acid)/acetonitrile gradient was used to generate baseline resolution and excellent peak shapes [963]. Linear curves from 100 to 5000ng/mL and quantitation limits of 150ng/mL were reported. ... 

Uliman ether synthesis.1 /n-Phenoxybenzyl alcohol (3) can be prepared by condensation of m-hydroxybenzyl alcohol (2) with chlorobenzene catalyzed by CuCl and 8-hydroxyquinoline (4). The yield is markedly dependent on the solvent, being highest in DMI. 

The effect of hydrotropes on the crossed Cannizzaro reaction rate of benzaldehydes with aqueous formaldehyde was investigated [67]. In the presence of polyethyleneglycol-200 the reaction rate of w-phenoxybenzalde-hyde increases more than six-fold and the w-phenoxybenzyl alcohol is also obtained with higher selectivity. The enhancement of the reaction rate of m-bromobenzaldehyde is lower than that observed for m-phenoxybenzaldehyde but the reaction selectivity is higher. p-Anisaldehyde and p-chlorobenzalde-hyde show an intermediate behavior. The cationic surfactants cetylpyri-dinium chloride and cetyltrimethylammonium bromide (CTABr) favor the Cannizzaro reaction instead of the crossed Cannizzaro one. 

---