Methyl anisole

Methyl anisole [104-93-8] M 122.2, h 175-176°, d 0.9757, n 1.512. Dissolved in diethyl ether, washed with M NaOH, water, dried (Na2C03), evaporated and the residue distd under vacuum. 

While discussing ethers we should mention that the presence of unreacted anisoles or methyl anisoles is highly undesirable in the manufacture of phenol-formaldehyde resoles. These materials tend to be unreactive relative to phenol under normal resole conditions. They are also volatile and have odors detectable at very low concentrations. They have been the source of worker complaints and costly claims in the wood products industry. Benzophenones and methyl phenyl ketones are also common phenol contaminants that are problematic in this regard. 

Display the electrostatic potential map for 2-methyl anisole. For which ring site, para to methyl or para to methoxy, is the electrostatic potential more negative Where do you expect electrophilic attack to occur Is your result consistent with the relative stabihties of intermediate benzenium ions formed upon addition of the electrophile Compare energies for 3-methyl-4-methoxybenzenium ion and 4-methyl-3-methoxybenzenium ion. 

Fora (4-Methyl anisole, p-Cresyl methyl ether, p-Methoxy toluene or Methyl-p-Cresol), colorl... 

Ortho (1,1-Azido methyl anisole), liq, bp 118° at 14mm of Hg. Prepd from a mixt of N-Nitroso-N-(2-methoxy-benzyl)-hydrazine and dil sulfuric acid by steam distn (Ref 1). Explodes when heated quickly (Ref 1) ... 

Para (4,4-Azido methyl anisole) prepn pro-per ties are in Beil... 

Mononitro Methyl Anisole (2-Nitro-4-methyl anisole, 3-Nitro4-methoxy l-methyl benzol or Methyl- [2-nitro4 methyl phenyl]-ether). CH3.0.(N02)C6H3.CH3, mw 167.18, N 8.38%, OB to C02-167.48%, pale yellow cryst, mp 8.5°, bp 274° (partial decompn), d 1.2025 g/cc at 25/4°, Rl 1.5536 si sol in eth (Ref 1). Prepd by heating K2-nitro-p-cresol with methyl-iodide methylalc in a sealed tube at 100°... 

Dinitro Methyl Anisole (4-Nitro-2-nitromethyl anisole, 3-Nitro-6-methoxynitromethyI toluol. or Methyl-[5-nitro-2-nitromethylphenyl] -ether). CH3.0.(N02)C6H3.CH2N02, mw 212.18, N 13.21%, OB to C02 —113.11%, cryst, mp 93—94°. Prepd from 4-nitro-2(lodomethyl) anisole in ether-ben2ene soln by treatment for 3 days at RT with Ag nitrate. The sodium salt explodes violently on heating Refs 1) Beil, not found 2) G. Bendy,... 

Trinitro Methyl Anisole (4,6-Dinitro-2-nitro-methyl-anisole, 3,5-Dinitro-6-methoxy-nitro-methyl toluol or Methyl-[4,6-dinitro-2-nitro-methyl phenyl]-ether). CH3.0.(N02)2C H2.— CH2N02, mw 257.18, N 16.34%, OB to C02 —77.77%, cryst, mp 65—66°. Prepd from 4-nitro 2-(mtromethyl)anisole by slow addition to a mixt of coned sulfuric-nitric acids (2 1) at 0° (Ref 2). Explodes violently when heated quickly (Ref 2)... 

Second-order rate coefficients (107fc2 at 25.0 °C) for a number of aromatics were benzene, toluene, m-xylene, and mesitylene, all > 1.0 anisole, 6.0 3-methyl-anisole, 200 2,3-dimethylanisoIe, 240 3,5-dimethylanisole, 3,800, and 1,3-di-methoxybenzene containing the following substituents H, 5,800 4-Br, 180 ... 

Tri nitrobutyl methyl anisole, c12H1sN307, mw 313.26, N 13.42%. Two isomers are described in the literature 2,4,6-TTinitro-5-(tert-butyl)-3 -methyl-anizole or 2,4,6-Trinitro-3-metboxy-5 -(tert-butyD-toluene. C4H. C6(NO2)3(CH3).0. ... 

CH3, It yel crysts, mp 88°. Can be prepd either by nitration of 5-(tert-butyl) 3-methyl-anisole with HN03 in Ac20 and then with mixed acid or by methylation of 5-(tert-butyl)-3-hydroxy-2,4,6 -trinitrotoluene with Me2S04(Refs 1, 2 3) and... 

The direct coupling of the tin enolate (175 Scheme 25) with (30) gives complex (176) in good yield (87%). Fortuitously, the bond formation gives approximately a 5 1 mixture in favor of the diastereomer required for trichothecene synthesis. Further elaboration of the major isomer leads to (i)-trichodiene (167), representing an eight step diastereoselective total synthesis of the natural product from p-methyl-anisole, which compares very favorably with previous methods.32-36... 

C7H7)+ Various including toluene, butylbenzene, benzyl chloride, xylene, benzyl alcohol, methyl anisole 29—46 g, m, P 185... 

Finally, 2,4,6-tricyanophenol m.p. 185° has been prepared from 2,4,6-tris-carboxy-methyl-anisol by an analogous route. It is a strong acid (pk 1.0) which can only be prepared from the pyridinium salt to give the phenol by cation exchange with lewatit S 140147 >. 

METHYL-o-ANISIDINE see MGO750 p-METHYL ANISOLE see MGPOOO 9-METHYLANTHRACENE see MGP750 METHYL ANTHRANILATE (FCQ see APJ250 N-METHYLANTHRANILIC ACID, METHYL ESTER see MGQ250... 

Methyl Anisole (Methyl methoxy benzene or Methoxytoluene). CH3.O.C5H4.CH3, mw 122.17, OB to CO2 —261.93%. Three isomers exist ... 

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