2, 3-Dichloro anisole

Eqn. (a) shows the interaction between thiophene-2-carboxylic acid chloride and 2, 3-dichloro-anisole in the presence of CS2, anhydrous aluminium chloride and subsequent hydrolysis yields [2, 3-dichloro-4-(2-thiophen carbonyl) phenoxy]-methyl (I). The methoxy function present in the latter reactant, being an ortho- and para-director, helps to hook on the thiophene-2-carbonyl moiety at the para-position of the 2, 3-dichloro anisole to give (I). Obviously, the ori/io-position is pre-occupied by a chloro group. 

Obtained by Friedel-Crafts acylation of 2,3-dichloro-anisole with p-methoxybenzoyl chloride in the presence of aluminium chloride at r.t. [979] or in benzene at 75-80° for 1 h (53%) [1288],... 

Obtained by reaction of acetyl chloride on 3,5-dichloro-anisole with aluminium chloride in refluxing carbon disul-C1 fide (30%) [1811]. 

Fluorescence Lifetimes. Fluorescence lifetimes were determined by the phase shift method, utilizing a previously-described phase fluorimeter. The emission from an argon laser was frequency doubled to provide a 257 nm band for excitation. Fluorescence lifetimes of anisole and polymer 1 in dichloro-methane solution were 2.2 and 1.4 nsec, respectively. Fluorescence lifetimes of polymer films decreased monotonically with increasing DHB concentration from 1.8 (0) to 0.7 nsec (9.2 x 10 3 MDHB). Since fluorescence lifetimes (in contrast to fluorescence intensities) are unaffected by absorption effects of the stabilizer, these results provide direct evidence in support of the intensity measurements for RET from polymer to stabilizer. 

Most of the side reactions have already been discussed in Section 26.1.3.3. (dediazoniation in organic solvents). Chlorinated aliphatic solvents, such as 1,2-dichloroethane and dichloro-methane, lead to an extensive formation of chloroaromatics, and aromatic solvents, even halogenated examples, can be arylated to some extent by arenediazonium tetrafluoroborates (vide supra). For example, during dediazoniation of benzenediazonium tetrafluoroborate in toluene, chlorobenzene, bromobenzene or anisole, 3-5 % of substituted biphenyls Ph-C6H4-X (X = Me, Cl, Br, OMe) are formed together with 0.5-0.8% of fluorobiphenyls.5 Fluorobiphenyls are formed through an ionic pathway (only 2- and 4-isomers are formed) whereas chlorobiphenyls result from a radical process (X = Cl, 2-/3-/4-isomer 26 47 27).243... 

A solution of 22.1 g 2-methyl-4-(methylthio)anisole and 17.5 g dichloro-methyl methyl ether in 600 mL CH2C12 was vigorously stirred, and treated with 24.5 g anhydrous aluminum chloride added portion-wise over the course of 1 min. Stirring was continued for 20 min while the color developed to a dark red. There was added 500 mL H,0 with caution, and stirring was continued until the initial yellow solids redissolved and there were two distinct phases formed. These were separated, and the aqueous phase was extracted with 3x100 mL CH,C12. The... 

Thus, p- xylene yielded 2,5-dichloro-p-xylene. The principal reaction with anisole was also chlorination and with phenol nitration when nitration temperature was low (-80°C) both o- and p- nitrophenols were formed. At room temperature chlorination also occurred yielding 2,4-dichloro-6-nitrophenol and 3,6-dichloro-2-nitro-phenol. 

Gallium(lll) oxide supported on MCM-41 mesoporous silica shows high catalytic activity with little or no moisture sensitivity in the acylation of aromatics wifh acyl chlorides. The cafalysf is utilized in 1,2-dichloro-ethane af 80°C for 3 h wifh differenf aromatic compounds, and aromatic as well as aliphatic acyl chlorides, giving ketones in 54%-82% yield. The activity order of fhe aromatic subsfrafes is benzene (43% yield) < toluene (50% yield) < mesifylene (71% yield) < anisole (79% yield), in agreement with the electrophilic substitution trend previously observed. This acylation reaction follows a probable redox mechanism similar to thaf described in Scheme 4.26. ... 

Anisole, 2,5-dichloro- Benzene, 1,4-dichloro-2-methoxy- 1,4-Dichloro-2-methoxybenzene 2,5-Dichloroanisole EINECS 217-852-6. 

In addition to its use in resins and adhesives, phenol is also the starting material for the synthesis of chlorinated phenols and the food preservatives BHT (butylated hydroxytoluene) and BHA (butylated hydroxy-anisole). Pentachlorophenol, a widely used wood preservative, is prepared by reaction of phenol with excess Cl2. The herbicide 2,4-D (2,4-dichloro-phenoxyacetic acid) is prepared from 2,4-dichlorophenol, and the hospital antiseptic agent hexachlorophene is prepared from 2,4,5-trichlorophenol. 

Dichloro-7-methoxy acridine may be prepared by the oxidation of 2,4-dichloro toluene and treating the resulting acid with 4-amino anisole at 220°C in the presence of KOH and w-butanol the additional compound when reaeted with either POCI3 or SOCI2 undergoes cyclization. One mole each of the side chain and the acridine residue get eondensed to yield the mepacrine base which on treatment with hydrochloric acid gives the offieial eompound. 

Thiophene-2-carboxylic 2, 3-Dichloro-acid chloride (156.5) anisole (177)... 

Srinivasan has described some chemical transformations of the 1,3-photoadducts of cis-l,3-dichloro(qfclobutene to benzene and anisole (611) and (612). Treatment of (611) with aqueous acid affords the alcohol (613), whose structure has been established by X-ray analysis of its p-nitrobenzoate ester. Oxidation of (613) gives the ketone (614), which is also produced by acid treatment of the anisole adduct (612). 

Formation energies of complexes of chloro- (and dichloro-) carbenes with unsaturated systems have been studied by ab initio calculation. Whereas isolated double bonds were found to react with carbenes, benzene proved to give weak but thermally stable complexes with and rj 7r-type interactions anisole gave two -complexes and an ylide structure. 

Preparation by oxidation of 2,2 -methylenebis(4-chloro-anisole) with chromium trioxide in refluxing acetic acid, followed by demethylation of the 5,5 -dichloro-2,2 -di-methoxybenzophenone so obtained with aluminium chloride in chlorobenzene at 60° for 5.5 h [295], (92%) [1320]. 

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