Phenetole p-

We have already mentioned the methyl and ethyl ethers of phenol, viz., phenyl methyl ether or anisole and phenyl ethyl ether or phenetole (p. 612). 

Ethers.—As phenol compounds, the amino phenols yield phenol ethers analogous to phenetole (p. 621). These ethers are themselves unimportant. 

Yield relative to p-chlorobenzoyl chloride (molar ratio phenetole p-chlorobenzoyl chloride = 4). 

Beilstein Handbook Reference) Benzene, 1-ethoxy-4-nitro- BRN 0972473 CCRIS 2333 EINECS 202-837-9 p-Ethoxynitrobenzene Ethyl p-nitrophenyl ether HSDB 5333 p-Nitrophenetol p-Nitrophenetole NSC 9812 Phenetole, p-nitro-. Prisms mp = 60° bp = 283° >.m 227, 307 nm (MeOH) slightly soluble in H2O, EtOH, soluble in petroleum ether, freely soluble in Et20, MezCO, CeHg. 

Diethyl ether, b.p. 35 . Di n-propyl ether, b.p. 90. Di propyl ether, b.p. 67 5. Anxsole methyl phenyl ether), b.p. 154 . Phenetole (ethyl... 

Bromine acetate has also been proposed310 as an intermediate species in the bromination of anisole, phenetole, and methyl p-tolyl ether by 2,4,6-tribromo-N-bromoacetanilide in acetic acid at 25 °C, since this latter compound was stable to both the ethers and to acetic acid, but in the presence of both, bromination of the ethers occurred, presumably via bromine acetate formed as in the equilibrium... 

FIGURE 9.4 Chromatograms of a reversed-phase test mixture. Plot A is the chromatogram at 30°C and ImL/min, and plot B is the chromatogram at 100°C and 5mL/min. Solutes 1, uracil 2, p-nitroaniline 3, methyl benzoate 4, phenetole 5, toluene. 2.1% (w/w) poly-butadiene coated zirconia column, mobile phase 20% ACN, flow rate was l.OmL/min at 30°C and 5mL/min at 100°C. detection 254 nm. (Reprinted from Li, J. et al., Anal. Chem., 69, 3884, 1997. Copyright 1997, American Chemical Society. With permission.)... 

Oglialoro modification of, 708 Perkin triangle, 108, 218f Kon modification of, 109 Peroxides, detection of, in ether, 163 removal from diethyl ether, 163 removal from isopropyl alcohol, 886 Petroleum ether, purification of, 174 Phenacetin, 996, 997 1 10-Phenanthroline, 991, 992 p-Phenetidine, 997, 998 Phenetole, 665,670 Phenobarbitone, 1003,1004,1005 Phenol, 595, 613 Phenol aldehyde polymers, 1016 formation of, 1022 Phenolphthalein, 984, 985 action as indicator, 984 ... 

The types of compound obtainable by the condensation of tellurium tetrachloride and mixed ethers may be exemplified by the case of phenetole. The primary product obtained in the reaction is p-phenetyl telluritriehloride (I), which on heating with more phenetole gives Ws-p-phenetyl telluridichloride (II). The latter also occurs if an excess of phenetole be used in the initial condensation. Reduction of the trichloride by aqueous potassium metabisulphite at 0° C. produces bis-p-phenetyl ditelluride (III). 

These compounds are suggested if sulphur is present. If nitrogen is also present the compound may be an aminosulphonic acid. The infrared spectrum will show absorption at 3400-3200 cm -1 (OH str.) and 1150 and 1050 cm-1 (S=0 str. in a sulphonic add) or at 1090cm-1 (S=0 str. in a sulphinic acid). For derivative preparations for sulphonic acids see Section 9.6.26, p. 1284. The presence of an aromatic sulphinic add may be further confirmed by dissolving in cold concentrated sulphuric add and adding one drop of phenetole or anisole when a blue colour is produced (Smiles s test), due to formation of a para-substituted aromatic sulphoxide. The reaction is ... 

C6HsO)t Phenol, phenetole, diphenyl ether, tropolone 480—578 g. n, p 456... 

C6H60)t Various precursors including phenol, phenetole, phenyl acetate, phenyl ether, acetophenone oxime 420-560 g, n, p 569... 

Slavinskaya [21] in 1957, found that phenol can be nitrated to o-, p- and 2,4-dinitrophenol using nitric acid dissolved in ethyl nitrate at a concentration as low as 0.5% HN03. Phenetole and naphthalene can also be nitrated with this solution to yield mononitro products. The presence of N02 was essential for successful nitration at such a low concentration of HN03. 

The quinonoid structure (see p. 202) is assigned to this product. It decomposes by the action of acids to yield trinitroanisole again. Boiling with ethyl alcohol converts the addition product into the analogous derivative of phenetole and sodium ethoxide (II). 

FIGURE 4-8. Comparison of optimized separation on phenyl and cyano (CN) phases compared to a C18 phase. Columns 8 mm ID x 10 cm Radial Pak cartridges containing Nova-Pak bonded phase, (a) Nova-Pak C18 using a mobile phase of acetonitrile water (35 65), and Nova-Pak phenyl using a mobile phase of methanol ace-tonitrile water (33 8 59). (b) Nova-Pak C18 using a mobile phase the same as in a and Nova-Pak CN using a mobile phase of tetrahydrofuran water (10 90). Flow rate 2 mL/min. Detection 254 nm. Sample 1. benzyl alcohol 2. 2-phenoxyethanol 3. anisaldehyde 4. acetophenone 5. p-tolualdehyde 6. p-methylacetophenone, 7. anis-ole 8. phenetole. 

SYNS 4-AMINOETHOX YBENZENE p-AMINO-FENETOL p-AMINOPHENETOLE 4-AMINO-PHENETOLE ANILINE, p-ETHOXY- BENZENAM-INE, 4-ETHOXY-(9CI) p-ETHOXYANILINE 4-ETHOXYANIUNE 4-ETHOXYBENZENAMINE p-FENETIDIN p-PHENETIDIN... 

I. Estermann, Zeitschr, /, phys. Chemie, B, 1, 153 (1928) gives — 10. from experiments on P as a function of T in benzene solution. As Hidjendahl has obtained a considerably larger value for anisole (i i6. io " ) than Estermann did (o-8. io , loc. cit.), it would be desirable to have the value for phenetole confirmed. 

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