Compounds phenetole

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... 

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 ... 

Hydrolysis of chloronitro compounds. The chlorine atom in chlorobenzene and in its homologues becomes reactive after one or more nitro groups have been introduced into the ring. This is used widely in the preparation of nitrophenols and their ethers. The preparation of dinitrophenol, dinitroanisole and dinitro-phenetole may serve as a classical example (see Chapter XVI). 

Tetranitroaniline is a rather unstable compound. Thus, when boiled with water its meta- nitro group undergoes hydrolysis to a phenolic group (II), while on boiling with methyl- or ethyl alcohol it yields an anisole- (III) or phenetole derivative (IV), which with ammonia may form trinitro-m-phenylenediamine (V) ... 

The following compounds are prepared in a similar manner, substituting toluene, anisole, phenetole, and diphenyl ether, respectively, for benzene ... 

These two ethers, known as anisole and phenetole, are well known compounds. 

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

When an alcohol is used as the reducing agent, the yield of deaminated aromatic compound is often very unsatisfactory owing to extensive formation of aryl ethers. Use of lower alcohols favors ether formation, whereas use of higher alcohols favors formation of the hydrocarbons for example, benzenediazonium chloride gives only anisole when methanol is used, a little benzene and much phenetole when ethanol is used, but much benzene and very little benzyl phenyl ether when benzyl alcohol is used. 

Dinitn>phenetole [610-54-8] M 240.2, m 85-86", 210-21 l"/15mm. Crystallise it from aqueous EtOH. The 1 1 naphthalene complex has m 41° and is obtained by fusing the compound with naphthalene in various ratios, then eiystallising the solidified mix from a little EtOH (Dermer Smith J Am Chem Soc 61 748 1939). [Beilstein 6 H 254,6 III 858,6IV 1373.]... 

The ether unit is another oxygenated frmctional group that can be attached directly to the benzene ring and, in most cases, the OR is treated as an alkoxy substituent (methoxy, ethoxy, butoxy, etc.). Therefore, 21 is called methoxyben-zene and 22 is ethoxybenzene. There are also common names for these compounds, so 21 is known as anisole and 22 is phenetole. 

Compounds (1) 2-phenylethylbromide, (2) 1,4-diphenylbutane, (3) phenetole, (4) nitrobenzene, (5) trans-chlorostilbene oxide, 6 = Sudan red 7B. 

Dithallation of some monocyclic aromatic compounds has been described. An excess of thallium(iii) trifluoroacetate in trifluoroacetic acid with thiophene gives the 2,5-dithallated product. Dithallation was also observed, to a lesser extent, for anisole, phenetole, toluene, i -xylene, and benzene. 

Trimethylanisole reacts with excess chlorosulfonic acid to give 4-methoxy-2,3,6-trimethylbenzenesulfonyl chloride this compound is used as a reagent for the protection of amino groups in peptide synthesis. Phenetole (ethyl phenyl ether, 187 R = Et), by reaction with chlorosulfonic acid (two equivalents) in chloroform yields the 4-sulfonyl chloride ° which is used in the preparation of heat sensitive recording materials. ... 

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