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United States Patent Office Patented Sept 3,833,677 United States Patent Office Patented Sept. 3, 1974 1. 2 3,833,677 in which Q represents a -CH=CH-, -CH=N-, PROCESS FOR THE PREPARATION OF SUBST -NH-, -S-, or -O-group; n1 is a whole number TUTED AROMATIC COMPOUNDS Charles Grard, Lyon, France, assignor to Rhone from 1 to 6 and n is 0 or a whole number from 1 to 5 Poulenc S.A., Paris, France (n not being greater than the total number of carbon No Drawing. Filed Feb. 25, 1970, Ser. No. 14,222 atoms in the aromatic ring and n2 being lower than the Claims priority, application France, Feb. 27, 1969, total number of carbon atoms in the aromatic ring); R1 690518S represents an aliphatic, cycloaliphatic or araliphatic hy nt. C. C07c 15/00 drocarbyl radical or an acyl radical each of which may U.S. C. 260-668 R 11. Claims be substituted by halogen (e.g. chlorine or bromine), or a O functional group such as nitrile, amino, nitro, nitroso, ABSTRACT OF THE DISCLOSURE amide, aldehyde, ketone, ester, ether, or a heterocyclic radical; R2 represents a radical which may be identical Friedel-Crafts-type condensation may be effected by with R1 or may be aryl, chlorine, bromine, hydroxyl, utilising, as catalyst, a derivative of ruthenium, rhodium, nitrile, nitro, nitroso, aldehyde, ether, or amine, or a hy osmium, or iridium, particularly a halide or halonitrile 5 drocarbon chain, which may be interrupted by one or complex, which catalyst may be used in conjunction with a more hetero atoms, forming a benzene or heterocyclic Brönsted acid catalyst. nucleus with two adjacent carbon atoms of the substituted nucleus; and when n is greater than 1 the several R2 The present invention provides a process for the prepara radicals may be identical or different, which comprises tion of aromatic compounds whose aromatic nuclei are 20 reacting a compound of the general formula: substituted by organic residues. A convenient method for the preparation of such aro R1-X; or matic compounds consists in replacing one or more hydro R-OH (R1 not being acyl); or gen atoms of the aromatic nucleus by the said organic (R1)2O (R1 being acyl) residue which is derived from a compound containing the 25 in which X represents halogen and R1 is as defined above, residue combined with one or more reactive functional with an aromatic compound of the general formula: groups, particularly halogen or hydroxyl. This class of reaction is known as a Friedel-Crafts condensation. Ex (R2)n amples of such condensations include alkylations and / acylations of aromatic compounds. To alkylate aromatic 30 compounds, reagents such as aliphatic halides, alkenes, alkynes or alcohols may be employed. To acylate aromatic in which n2, Q and R2 are as defined above. compounds, reagents such as acid chlorides, acid anhy More specifically, R may be alkyl of 1 to 10 carbon drides, esters or carboxylic acids may be employed. The atoms, such as methyl, ethyl, propyl, isopropyl, n-butyl, aforementioned reactions of aromatic compounds are of sec-butyl, tert-butyl; aralkyl of 7 to 20 carbon atoms, such considerable industrial value because of the large number as benzyl, phenylethyl, naphthylmethyl, piperonyl; alkenyl of products which may be obtained from them. For ex of 2 to 10 carbon atoms, such as vinyl, allyl, propenyl, ample, acylation of aromatic compounds allows aromatic butenyl; cyclohexyl or cyclohexenyl; hydroxyalkyl, such ketones and aldehydes (using, in this case, for example as hydroxyethyl, hydroxypropyl, hydroxybutyl; alkoxy-, CO and HCl) such as acetophenone, propiophenone and 40 cycloalkoxy-, cycloalkenyloxy- or arylox-alikol, such as a-chloracetophenone to be prepared. ethoxyethyl, propoxyethyl, vinyloxyethyl, allyloxyethyl; To carry out the alkylation and acylation of aromatic acyl, such as acetyl, propionyl, butyryl, acrylyl, methacryl compounds by Friedel-Crafts condensation, acid catalysts yl, benzoyl, toluyl. R2 may, in addition to the above-men are employed. Either Brönsted acids, such as HF, HCl, 45 tioned radicals, be alkoxy, such as methoxy, propoxy, eth H2SO4 or HaPO4 or Lewis acids, such as metal or boron oxy; cycloalkoxy, such as cyclohexyloxy; aryloxy, such as halides may be used. The metal halides are those of phenoxy; alkenyloxy, such as allyloxy; or aryl, such as metals in most groups of the periodic classification, but phenyl. the aluminium halides, such as aluminium cholride or As the substituting compound of formula R1-X, aluminium bromide, are most used. BeCa, CdCl2, ZnCl2, 50 R-OH or (R)O substituted or unsubstituted aliphatic, CrCl3, TiCl4, ZnCl4, SnCl4 and FeCls are other metal cycloaliphatic or araliphatic chlorides or bromides, such halides which can be used in the Friedel-Crafts con as methyl, ethyl, propyl, isopropyl, sec-butyl, tert-butyl, densation. However, the halides of the noble metals of cyclohexyl, benzyl chloride or bromide, bis-(chloro group VIII of the periodic classification have never methyl) benzene, ethoxyethyl chloride, allyloxyethyl chlo hitherto been used as catalyst in this condensation. 55 ride, phenoxyethyl chloride, allyl chloride, propenyl chlo According to the present invention, there is provided a ride, methallyl chloride, piperonyl chloride, chloro- and process for the preparation of an aromatic compound sub bromo-methylnaphthalene; substituted or unsubstituted stituted by a substituted or unsubstituted, aliphatic, cyclo aliphatic, cycloaliphatic or araliphatic primary or second aliphatic or araliphatic hydrocarby radical or an acyl ary alcohols, such as ethanol, propanol, cyclohexanol, radical which comprises reacting an aromatic compound 60 benzyl alcohol, 6-phenylethyl alcohol, methoxyethanol, containing at least one hydrogen atom attached to an aro ethoxyethanol, or allyloxyethanol; acyl halides such as matic nucleus with a substituted or unsubstituted, aliphatic, acetyl, propionyl, butyryl, acrylyl, methacrylyl, benzoyl, cycloaliphatic, or araliphatic halide or alcohol, an acyl toluyl, chlorides and bromides; and acid anhydrides such halide, or an acid anhydride in the presence of, as catalyst, as acetic, propionic and benzoic anhydrides, may be used. a ruthenium, rhodium, osmium, or iridium compound. 65 As the aromatic compound to be substituted benzene, More particularly, the present invention provides a toluene, ethylbenzene, xylenes, isopropylbenzene, allyl process for the preparation of an aromatic compound of benzene, trimethylbenzenes, naphthalene, biphenyl; phe the general formula: nols such as phenol, cresols, pyrocatechol, alkoxyphenols, such as guaiacol, guaiethol; phenol ethers such as anisole, N SR), 70 phenetole, trimethoxybenzenes, dimethoxybenzenes, allyl oxybenzene, 1,2-methylenedioxybenzene; and aldehydes, X > such as benzaldehydes, may be used. 3,833,677 3. 4. Besides obtaining benzenoid aromatic compounds, the EXAMPLE 1. process also applies to the introduction of R groups into The apparatus used consisted of a 100 cm.8 round 3 heterocyclic aromatic compounds, such as thiophene. necked flask equipped with a dip tube, gas inlet, a reflux As examples of catalysts, halides of Ru, Rh, Os and Ir, condenser, a dropping funnel, a thermometer and an oil Such as RuCl3, RhCl3, OsCl3, IrCl3, RuBr3, RhBr3, OsBr3, bath. The reflux condenser was connected to a conica IrBra and Rula in the anhydrous or hydrated form are 125 cm.8 flask equipped with a dropping funnel contain preferably used. It is also possible to employ halogenated ing a 1N aqueous solution of sodium hydroxide. The coni complexes of these metals obtained from a metal halide cal flask contained water and a tube connecting it to the and a monodentate or polydentate ligand, for example, condenser opens into the aqueous layer. The contents of those described in French Pat. 1,505,334 and its addition O the round flask and of the conical flask were stirred with No. 91,167. More particularly, the following nitrilo com a magnetic stirrer. plexes: dichloro-tetrakis(acrylonitrilo)ruthenium, dichlo 44.2g. of toluene (0.48 mol) and 0.322 g. of ruthenium ro-tetrakis(methacrylonitrilo) ruthenium, diiodo-tetrakis chloride, obtained according to the method of K. D. Hyde (acrylonitrilo)ruthenium, dichloro-tetrakis (benzonitrilo) et al.; J. Less Common Metals, 8, 428 (1965) by chlorina ruthenium and trichloro-tris(acetonitrilo)ruthenium may tion of ruthenium at a temperature above 450 C., and be used. exhibiting the X-ray characteristics of the or crystalline The amount of catalyst, expressed in mols of metal form, were introduced into the round flask. 15.8 g. (0.125 compound per mol of substituting compound may vary mol) of benzyl chloride were introduced into the dropping within wide limits. Generally, an amount of between funnel, and a stream of hydrogen chloride gas was then 10 and 5X10 mol of metal derivative per mol of sub 20 passed into the toluene, heated to the reflux temperature stituting compound is very suitable, but it is possible to use for about 15 minutes at a rate of 0.1X10-2 mol/minute higher ratios, for example equal to 1 or greater than 1. under normal conditions of pressure and temperature. The catalyst may be used by itself or be deposited on a Thereafter, the benzyl chloride was gradually introduced carrier such as those generally employed in catalysis (alu into the flask over the course of 5 hours, after having re mina, silica, asbestos, clay, pumice and animal and vege placed the stream of hydrogen chloride by a slight stream table charcoals). At the end of the reaction, the catalyst of nitrogen. The mixture was kept under these conditions may be recovered by the usual methods and recycled to a for 1 hour and then cooled, and the residual hydrogen Subsequent operation. chloride was driven off by a strong stream of nitrogen. Regardless of the metal derivative used as the catalyst, a The reaction mixture was then filtered to remove the Brönsted acid such as HCl, HF, HSO, HPO, or a sul 30 ruthenium chloride, and the filtrate was thereafter washed phonic acid may simultaneously be used. The amount em with a 1N aqueous solution of sodium bicarbonate until ployed may vary within a wide range but it is generally neutra.
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