2-Phenoxypropane

Bromine (2 moles) in carbon tetrachloride was added to a stirred solution of 2,2 -(azo-2-phenoxypropane) and phenol in acetonitrile at ambient temp, and the mixture worked up after a few mnis. to give 2-bromophenol. 

Our results conci red with those above when 3-bromo-l-phenoxypropane was added to our Mg at room temperature the reaction was quite vigorous(40). Upon carbonation, followed by hydrolysis, the only acidic product isolated was phenol in 70% yield. It was very satisfying to note that at -78 °C the reaction of 3-phenoxypropyl bromide proceeded smoothly. 

Although some workers have found difficulty in purifying the product, a particularly convenient preparation of chroman involves the cyclization of l-chloro-3-phenoxypropane in the presence of tin(IV) chloride (equation 11) (52CR(234)1787). The synthesis is readily adapted to give many substituted chromans. A surprising result was obtained using 3-chloro-... 

Table 4 Cyclization of Some m-Substituted 1,3-Diphenoxypropanes and 3-Phenoxypropan-l-ols...

A variation on this general theme which has not been as widely applied as the previous examples, but which is nevertheless of value, involves the use of 3-phenoxypropan-l-ols (66JOC3032, 67JCS(B)859). Here again it is observed that the m-substituted isomer cyclizes to a mixture of two chromans. 

This mixed reactivity is illustrated by the results of a recent reinvestigation of the reaction between 4-chloro-methyl-l,3,2-dioxathiolane K-oxide 33 and sodium phenoxide in ethanol (Scheme 3) <2000IZV1774, 2000RCB1753>. 3-Phenoxypropane-l,2-diol 35 has been obtained as the major product (45%), while only traces of... 

The conversion of dextran with 1,2-epoxy-3-phenoxypropane, epoxyoctane or epoxydodecane may be exploited for the preparation of amphiphilic dextran derivatives. Polymeric surfactants prepared by hydrophobic modification of polysaccharides have been widely studied, starting with the pioneering work of Landoll [261]. Neutral water-soluble polymeric surfactants can be obtained by reaction of dextran with 1,2-epoxy-3-phenoxypropane in 1 M aqueous NaOH at ambient temperature (Fig. 35, [229,233]). The number n of hydrophobic groups per 100 Glcp units varies between 7 and 22 depending on the reaction conditions. 2-Hydroxy-3-phenoxy propyl dextran ethers (DexP) behave like classical associative polymers in aqueous solution. In dilute solution, the intrinsic viscosity decreases significantly whereas... 

SYNS 688A BENSYLYT 2-(N-BENZYL-2-CHLOROETHYLAMINO)-l-PHENOXYPROPANE HYDROCHLORIDE BENZYL(2-CHLOROETHYL)(l-METHYL-2-PHENOXYETHYL)AMINE HYDROCHLORIDE N-BENZYL-N-PHENOXYISOPROPYL-P-CHLORETHYLAMINE HYDROCHLORIDE ... 

SYNS l,2-EPOXY-3-PHENOXYPROPANE 2,3-EPOXYPROPYLPHENYL ETHER FENYL-GLYCIDYLETHER (CZECH) GLYCIDYL PHENYL ETHER PGE PHENOL-GLYCIDAETHER (GERMAN)... 

In the preparation of 2-phenoxymethylperhydro-imidazo[l, 2-a]pyridine (221), the ring opening of 1,2-epoxy-3-phenoxypropane (219) with 2-aminopyridine followed by catalytic reduction of the hydrochloride of the resultant amino alcohol over Rh/C gave 220. Treatment of220 with thionyl chloride followed by base produced the required 221 (70IJC707). 

The poiyether poiy(bisphenol F digiycidyi ether) shows a weight ioss as low as 80° C in NaOH [23]. Some other poiyethers are described in literature, such as poly[bis(2,3-epoxy-cyclopentyl)ether], poly(1,4-butandioi digiycidyi ether), poly(phenyl glycidyi ether), poly(1,2-epoxy-3-phenoxypropane), etc. The structures of the main sequence of these poiymers after curing are shown beiow ... 

Hydrogen halides Acetamide. Ammonium acetate. Ammonium formate. Epichloro-hydrin. l,2-Epoxy-3-phenoxypropane. Ethylenediamine. Ethylene oxide. Magnesium oxide. Propylene oxide. 

Regioselective hydroxylation of aromatic compounds can also be achieved by using whole cells. For instance, 6-hydroxynicotinic acid (35) is produced industrially from nicotinic acid (34) by a Pseudomonas or Bacillus sp (equation 48) . Racemic prenalterol (37) has been obtained by regioselective p-hydroxylation of ( )-l-isopropylamino-3-phenoxypropan-2-ol (36) using Cunninghamella echinulata (equation 49) . 

The reaction between the epoxy and the end groups of the polyester was modeled by using l,2-epoxy-3-phenoxypropane and n-octanoic acid. An equimolar solution of the two was prepared in tetrahydrofuran (THF) with a catalytic amount of pyridine a few drops of this solution were placed on a NaCl window and the THF allowed to evaporate. The reaction was carried out at 100 °C, and the IR spectrum of the mixture was recorded every 15 min. Similar experiments were performed without a catalyst. The reaction between... 

Figure 2. Infrared spectrum of a mixture of l,2-epoxy-3-phenoxypropane and n-octanoic acid at 100 °C as a function of time, showing the rapid disappearance of acid carbonyl absorption in the presence of pyridine as a catalyst.

An early example by Reetz and co-workers [79] demonstrated the evaluation of a series of biocatalysts for the hydrolytic kinetic resolution of chiral glycidyl phenyl ethers. Employing a fused-silica reactor, the authors developed an integrated reaction system capable of performing biocatalytic hydrolysis, along with separation and detection of the reaction products. Using the enantioselective hydrolysis of 2-phenoxymethyloxirane (136) to 3-phenoxypropane-l,2-diol (137) as a model reaction (Table 6.14), the authors evaluated the biocatalytic activity of a series of epoxide... 

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