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UNITED STATE S PATENT OFFICE Patented Nov. 26, 1946 2,411,516 s PATENT OFFICE UNITED STATE 2,411,516 ETHERS OF ENDOETHYLENE-SUBSTITUTED CYCLOPENTANOLS Herman A Bruson, Philadelphia, Pa., assignor to The Resinous Products & Chemical Company, Philadelphia, Pa., a corporation of Delaware No Drawing. Application May 24, 1944, Serial No. 537,183 8 Claims. (C. 260-61) 2 This invention relates to addition-rearrange acetate, allyl oleate, vinyl methyl ketone, vinyl ment products from organic compounds having acetate, vinyl benzoate, and the like. There may alcoholic hydroxyl groups and adducts of cyclo also be used other adducts of cyclopentadiene pentadiene with mono-olefinic compounds hav with olefinic compounds, such as courmarOne, ing at least three carbon atoms, said products safrole, eugenol, and with allyl ethers, Such as being ethers of an endoethylene-substituted cy benzyl allyl ether, phenyl allyl ether, Octyl allyl clopentanol. ether,In practicing and the like. this invention, it has been found In my copending application, Serial No. 476,- that a wide variety of organic compounds con 640, filed February 20, 1943, it is shown that non taining one or more alcoholic hydroxyl groups resinous polycyclopentadienes having two double 0 may be employed. The hydroxyl group is pref bonds per molecule, such as dicyclopentadiene, erably primary or secondary. Compounds con tricyclopentadiene, and tetracyclopentadiene add taining a tertiary hydroxyl group may also be alcohols in the presence of acidic condensing used, provided, however, that they are not readily agents to form addition-rearrangement products dehydrated. f which are ethers of a new ring System termed 5 The useful alcoholic hydroxyl-containing com the 'nordicyclopentadiene' ring system. pounds may be aliphatic, arylaliphatic, cycloali In accordance with the present invention, phatic, hydroaromatic, or heterocyclic and may which is a continuation-in-part of copending ap be saturated or unsaturated, straight- or plication Serial No. 529,195, filed April 1, 1944, branched-chained, or cyclic. It has also been adducts of cyclopentadiene with mono-olefinic 20 established that the non-hydroxyl portion of the compounds having at least three carbon atoms in reacting hydroxyl-containing compound may the molecule are reacted with alcohols in the contain a wide variety of groups or substituents, presence of acidic condensing agents to form ad for example, halogen, cyano, thiocyano, nitro, dition products which are rearranged ethers keto or acyl, mercapto, ether, acyloxy, alkoxy, from endo-ethylene-substituted cyclopentanols. 25 aryloxy, carbalkoxy, or carboxy groups, etc. A typical illustration is that, for example, in It should be noted at this point that, in the volving the action of an alcohol, ROH, upon the case of alcoholic hydroxyl-containing compounds cyclopentadiene-styrene adduct, having free carboxyl groups, excess cyclopenta 30 diene-olefine adduct is necessary since esterifica cf CB off? R CH, tion of the carboxyl group by addition and simul ROH . taneous rearrangement occurs in addition to CE seamed CH etherification with the alcoholic hydroxyl group. C CE-CBIs R-O-CH----C-CI From the above discussion, it will be evident N f that under the influence of acidic condensing C CE 35 agents cyclopentadiene-olefine adducts of the The product formed by the molecular addition rearrangement is very probably that represented type set forth form rearranged ethers with a wide by formula (A). In any event, the product is not variety of alcoholic hydroxyl-containing com a simple addition of (R-O-) to one side of the pounds and that the reaction is one of wide ap double bond and of H to the other. The reaction 440 plicability. Hydroxyl-containing reactants of involves both addition and rearrangement and perhaps greatest interest belong to the general leads to a new class of substituted cyclic Com class of unsubstituted alcohols, whether mono pounds which are not available by any previously hydric or polyhydric, which are not dehydrated proposed method of synthesis. at 60° C. by sulfuric acid. There are, however, Warious adducts of cyclopentadiene with mono 45 importantple alcohols. types Other of reactants important other groups than includehy the sim olefinic compounds having three or more carbon droxy-acid esters, hydroxy-acids, hydroxy-ke atoms in the molecule may be used for the pur tones, hvdroxy-lactones, hydroxy-aldehydes, pose of this invention. These comprise not only the so-called "Diels-Alder' type of adducts of ether alcohols, cyano alcohols, thiocyano alco cyclopentadiene with unsaturated hydrocarbons 50 hols, halohydrins, nitro alcohols, and polymeric as, for example, propylene, cyclopentene, styrene, hydroxyl-containing compounds, including poly indene, allylbenzene, and the like, but also the vinyl alcohol, polysaccharides, starches, sugars, adducts of cyclopentadiene with unsaturated al cellulose, cellulose ethers, cellulose esters, and the cohols, esters, halides, or ketones, as, for example, like. allyl alcohol, allyl chloride, allyl benzoate, allyl 55 Typical wseful hydroxyl-containing com 2,411,516 - 3 . 4 pounds for the purpose of this invention are the toluene sulfonic acid, or aliphatic sulfonic acids, following: methanol, ethanol, propanol, iso as butylsulfonic acid and the like. propanol, n-butanol, isobutanol, butanol-2, the Sulfuric acid is of particular value in promot primary and various isomeric amyl alcohols, n ing reactions involving the lower primary hexanol, 2-ethylbutanol, n-heptanol, n-Octanol, aliphatic alcohols. It is generally of use in the capryl alcohol, 2-ethyl hexanol, decanol, 5 case of other alcohols also, which are not readily ethyl-nonanol-2, dodecyl alcohol, tetradecanol, 7 polymerized) or dehydrated by the presence of ethyl-2-methyl-undecanol-4, cetyl alcohol, 39 concentrated sulfuric acid. diethyl-tridecanol-6, oley alcohol, n-octadecanol, The boron trifluoride group of catalysts is one allyl alcohol, crotonyl alcohol, cinnamyl alcohol, 0. of considerable value. Of these, the complexes geraniol, phenylethyl alcohol, methoxyethanol, with ethers are of particular utility since they ethoxyethanol, butoxyethanol, phenoxyethanol, are soluble in the reaction mixtures and pro ethylene glycol, propylene glycol, butylene gly duce no troublesome by-products. Typical of col-1,3, diethylene glycol, triethylene glycol, these complexes are BF.C2H-O-Cahs and polyethylene glycols, di-isopropylene glycol, di 5 BF.C4H-O-C4Ho, with diethyl ether and di ethylene glycol monoethyl ether, diethylene n-butyl ether, respectively. glycol monobutylether, diethylene glycol mono The quantity of active catalyst employed may phenylether, glycerol, glycerol monochlorohy be varied over a wide range. Good results have drin, glycerol dichlorohydrin, glyceryl-a-phenyl been obtained with as little as two per cent of ether, 2-ethyl -hexandiol - 1,3, glyceryl - ox,y- 20 catalyst, based on the Weight of the cyclopenta dimethyl ether, trimethylene glycol, tetramethyl diene adduct, up to and exceeding a molar equiv ene glycol, decamethylene glycol-1,10, pentaery alent of the catalyst permol of adduct used. The thritol, ethylene? chlorohydrin, propylene chloro catalysts need not be used under anhydrous con hydrin, ethylene bromohydrin, propargyl alcohol, ditions. In fact, the presence of water in small ethylene cyanohydrin, p - thiocyanophenoxy 25 amounts often increases the rate of reaction. ethanol, 2-nitro-2-methyl-1-propanol, 3 - thio The addition-rearrangement reaction involv cyanoethoxyethanol, p - tertiary-butylphenoxy ing an alcoholic hydroxyl-containing compound ethanol, o - cyclohexylphenoxyethanol, 2,4-di and the adduct of cyclopentadiene and a mono-, chlorophenoxyethanol, p - ter - octylphenoxy olefinic compound is readily carried out in the ethanol, plphenylphenoxyethanol, 3-naphthoxy 30 presence of one or more acidic condensing agents. ethanol, 2 - nitrophenoxyethanol, p - acetyl The reaction may be initiated by mixing the phenoxyethanol, p-benzoylphenoxyethanol, cyclo components and catalyst at room temperature, hexanol, o-, m-, or p-methylcyclohexanol, cyclo at temperatures even around 0° C. in some cases, pentanol, o- or p-cyclohexyl-cyclohexanol, p-tert or at elevated temperatures. While it is genera amylcyclohexanol, hydroxydihydronordicyclo ally desirable to control the temperature at the rentadiene, borneo, fenchol, cholesterol, ethyl start, the reaction may be carried to completion glycolate, ethyl lactate, dimethyl tartrate, ethyl either by continuing the reaction for a long time citrate, benzyl alcohol, 2-nitro-2-methyl-1,3- or by raising the temperature to accelerate the propanediol, ethyl-10-hydroxy-stearate, tetrahy reactions involved. Temperatures as high as 100° drofurfuryl alcohol, phenyl thioethanol, ceryl 40 C. to about 200° C. may thus be used. The re alcohol, 2-nitro-2-ethyl-1,3-propanediol, castor action range of about 50 to 125° C. is, however, oil, hydrogenated castor oil, ethyl ricinoleate, generally the most useful and is to be preferred. ethyl maleate, sorbitol, dibutyl tartrate, glyceryl In Some cases the reactions are sufficiently or, y-diphenyl ether, mannitol, ethylene glycol exothermic that it is desirable to cool the react monobenzylether, and many others. The hy ing mixture in order to control the reaction. droxyl-containing compound need not be pure. This may also be controlled by the rate of mix There may be used, for instance, technical al ing the reactants and by the use of a solvent or cohol mixtures such as are obtained as by-prod diluent such as
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