Phenetol

Add 2 mi. of ethanol to the solution, shake the mixture and warm gently. Phenetole (ethyl phenyl ether) is the main product. 

Phenetole. (Ethyl Phenyl Ether.) CeHsOCaHj. (Method i,... 

In view of the high cost of methyl iodide in the above preparation of anisole, and the fact that, unless absolute methanol is used, the ready hydrolysis of the methyl iodide may cause a low yield of the ether, the preparation of anisole may be ad antageously replaced by that of phenetole. I he reaction is not of course a methylation, but is nevertheless of the same type as that used in the preparation of anisole. 

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... 

Sulphinic acids. Aromatic sulphinic acids are found in Solubility Group II. They may be detected by dissolving in cold concentrated sulphuric acid and adding one drop of phenetole or anisole when a blue colour is produced (Smiles s test), due to the formation of a para-substituted aromatic sulphoxide. Thus the reaction with benzenesulphinic acid is ... 

Warm the substance with a few c.c. of ethyl alcoliol. Vigorous effervescence occurs and the liquid turns red. Wlaen effervescence ceases, add water. An oil separates out on tlae surface consisting of benzene mixed with a little phenetol. 

This ether, C iHg. O. CgHg, is known as phenetole. It is a fragrant liquid boiling at 172°, and is prepared in a similar manner to the methyl ether. 

DinitropheneioiB. Light yel leaflets from ale, mp 101°. Was prepd by Blanksma (Ref 2) by the deammination of 2,3-dinitro-4-amino-phenetole... 

Dinitrophenetole- Crysts, mp 96-98° was prepd by dearomination of 2)5-umitro-4-ainino-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 kinetics of bromination with the complex formed between bromine and dioxan have been examined using benzene (which is unattacked) as solvent311, and it is probably appropriate to regard this as a catalysed bromination in view of the effect of dioxan upon the polarity of the bromine-bromine bond. With anisole, phenetole, and isopropoxybenzene, third-order kinetics are obtained, viz. 

Smith et al. (1998) have reported selective para acetylation of anisole, phenetole, and diphenyl ether with carboxylic anhydrides at 100 °C, in the presence of catalytic quantities of zeolites H-beta. The zeolite can be recovered and recycled to give essentially the same yield as that given by fresh zeolite. 

Heating pyridine-2,3-dicarboxylic acid anhydride with l-ethyl-2-methylindole has been claimed to yield solely the pyridine-2-carboxylic acid, albeit in low yield. This then clearly reacts with Af,A/-diethyl-3-toluidine in acetic anhydride to give the 7-azaphthalide. This is surprising in view of a later report70 in which a one-pot process has been described. Heating pyridine-2,3-dicarboxylic anhydride, prepared in situ, with the indole and subsequent reaction with 3-/V,/V-diethylamino-phenetol under identical conditions to those used in Scheme 8 (but without intermediate isolations) produced a 20 1 mixture of the 4- and 7-azaisomers 16 and 17. It appears that in the previous report the major intermediate isomer, the pyridine-3-carboxylic acid, has not been isolated. 

The base-catalyzed intramolecular cyclization of appropriately substituted 4-alkyn-1-ols, followed by in situ Claisen rearrangement, has been investigated by Ovaska and coworkers (Scheme 6.85) [179]. The tandem cydization-Claisen rearrangements were best carried out in N,N-dimethylformamide or phenetole as solvent in the pres-... 

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