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United States Patent (19) 1 L) 3,943,177 Helmlinger Et Al

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United States Patent (19) 1 L) 3,943,177 Helmlinger Et Al United States Patent (19) 1 l) 3,943,177 Helmlinger et al. (45 Mar. 9, 1976 (54) COMPOUNDS OF THE SINENSALTYPE, INTERMEDIATES AND PROCESS (56) References Cited THEREFOR UNITED STATES PATENTS (75) Inventors: Daniel Helmlinger, Dubendorf, 3,456,015 7/1969 Marbet............................ 260/593 R Peter Naegeli, Wettingen, both of 3,574,715 4/1971 Marbet et al................... 260/593 R Switzerland OTHER PUBLICATIONS (73) Assignee: Givaudan Corporation, Clifton, N.J. Thomas, J. Am. Chem. Soc., 91, June 1969, pp. 3281-3288. 22) Filed: Mar. 2, 1973 (21 Appl. No.: 337,341 Primary Examiner-James O. Thomas, Jr. Assistant Examiner-James H. Reamer (30) Foreign Application Priority Data Attorney, Agent, or Firm-Thomas Cifelli, Jr. Mar. 10, 1972 Switzerland......................... 35.10/72 57 ABSTRACT (52) U.S. Cl...... 260/593 R; 260/638 R; 260/632 R; Flavorants and fragrance materials of the sinensal 260/654 R; 260/657; 260/601 R; 260/614 R type, novel halides, alcohols, and ketones intermedi (51) Int. Cl.'.......................................... C07C 49/20 ates and process for making same. (58 Field of Search ................................. 260/593 R 1 Claim, No Drawings 3,943, 177 2 wherein R has the significance given earlier. COMPOUNDS OF THE SINENSALTYPE, INTERMEDIATES AND PROCESS THEREFOR DESCRIPTION OF THE PREFERRED EMBODIMENTS FIELD OF THE INVENTION 5 The oxidation of a compound of formula II can be This invention relates to the fields of flavorants and carried out according to methods known per se. fragrances. A preferred oxidation method comprises the treat ment of a halide of formula II with an alkali salt of a SUMMARY OF THE INVENTION primary or secondary nitroalkane; that is to say, of a This invention is concerned with a process for the () compound which can form an aci-form. Examples of manufacture of compounds of the sinensal type of the suitable nitroalkanes are nitromethane, nitroethane general formula and 1- or 2-nitropropane, with 2-nitropropane being OHC-. C(CH) scCH-CH-CH-COCH)= preferred and being used in the form of the sodium or CH-CH-A potassium salt. 5 The oxidation can be carried out in the presence of wherein A represents a group of the formula anhydrous or aqueous organic solvents; for example, a mono or polyhydroxy alcohol such as ethanol, isopro -CH-C(=CH)-CH=CH, panol, tertbutanol or mono- or diethylene glycol, a O water-soluble ether such as diethylene glycol ethyl butyl ether, dioxan or tetrahydrofuran, a dialkyl amide such as dimethylformamide, an acetal such as methylal, An especially interesting comopund of formula I a ketone such as acetone, acetonitrile etc. The oxida manufactured in accordance with the present invention tion components are preferably stirred in the solvent at is trans-trans-2,6-dimethyl-10-methylene-dodeca a temperature between -10°C and 80°C. In a preferred 2.6, ll-trienal (g-sinensal) which occurs in natural 25 embodiment of the process, a nitroalkane (e.g. 2-nitro orange oil. propane) is dissolved in a mixture of an organic solvent The process in accordance with the present invention (e.g. dimethylformamide, isopropanol or acetone) and for the manufacture of the compounds of formula I aqueous sodium hydroxide or potassium hydroxide, a comprises oxidising a halide of the general formula 30 halide of formula II is added to the resulting solution of Hall-CH-CCH)=CH-CH-CH-COCH)= the sodium or potassium salt of the nitroalkane and the CH-CH-A mixture is stirred with heating to about 50-80°C. In another suitable embodiment of the process, a solution wherein A has the significance given earlier and Hal of an alkali alcoholate such as potassium tertbutylate in stands for a chlorine or bromine atom. 35 tertbutanol, can be added to a nitroalkane and the The halide starting materials of formula II are novel resulting solution or suspension of the alkali salt of the and also form part of the present invention. They can nitroalkane can be stirred with a halide of formula II at be prepared, also in accordance with the present inven -50°C. A nitroalkane can also be introduced into a tion, by treating an alcohol of the general formula suspension of finely divided anhydrous potassium hy 40 droxide in an acetal such as methylal or an ether such as diethylene glycol ethylbutyl ether and the mixture obtained can be stirred with a halide of formula II at wherein A has the significance given earlier, with an room temperature. Depending on the alkalisalt and the appropriate halogenating agent. solvent used, there is obtained a homogeneous solution The alcohols of formula III are also novel and form 45 or a mixture which separates into two layers. In the part of the present invention. They can be prepared, latter case, it is expedient to bring about an intimate also in accordance with the present invention, by re mixture of the two phases by intensive stirring. ducing a ketone of the general formula The halide starting materials of formula II are novel HC=C(CH-CO-CH-CH-COCH)= and also form part of the present invention. They can CH-CH-A IV 50 be prepared, also in accordance with the present inven tion, by treating an alcohol of the general formula wherein A has the significance given earlier. The ketones of formula IV are also novel and form HCFC(CH)-CHOH-CH-CH-COCH)= part of the present invention. They can be prepared, CH-CH-A also in accordance with the present invention, by the 55 wherein A has the significance given earlier, with an acid-catalysed reaction of a vinyl carbinol of the gen appropriate halogenating agent. eral formula The treatment of an alcohol of formula III with an HC=C(CH)-CHOH-CH-A W appropriate halogenating agent can be carried out in a manner known per se. Suitable halogenating agents wherein A has the significance given earlier, with an 60 include, for example, hydrogen halides (e.g. hydrogen enol ether of the general formula bromide), phosphorus halides (e.g. phosphorus tribro mide and phosphorus pentachloride) and thionyl chlo ride. Thionyl chloride is preferred. wherein R represents a lower alkyl group, or a corre 65 The alcohols of formula III are also novel and form sponding ketal of the general formula part of the present invention. They can be prepared, also in accordance with the present invention, by re HC-C(CH)-C(OR)-CH W ducing a ketone of the general formula 3,943,177 4 reaction, the alcohol formed during the reaction distill CH-CH-A IV ing off therewith. The reaction is preferably carried out at an elevated wherein A has the significance given earlier. temperature; for example, at a temperature above 50°C The reduction of the oxo group in a ketone of for 5 and especially at the reflux temperature of the reaction mula IV to a hydroxy group can be carried out in a mixture. The reaction can be carried out under normal manner known perse using a suitable reducing agent pressure or under excess pressure. It is preferred to such as a complex alkali metal hydride (e.g. lithium carry out the reaction under the atmosphere of an inert aluminum hydride, sodium aluminium hydride or so gas (e.g. nitrogen or argon). r dium borohydride), a complex trialkoxy-alkali metal O hydride (e.g. trimethoxy lithium aluminum hydride or The following Example illustrates the present inven tritertbutoxy lithium aluminium hydride), a substituted tion: . aluminium hydride (e.g. diethyl aluminium hydride or Example disobutyl aluminium hydride) or a trialkyl compound a. A solution of 7 g of 2-methyl-6-methylene-octa (e.g. triisopropyl aluminium). Complex alkali metal 15 1,7-dien-3-ol and 14 g of 3,3-dimethoxy-2-methyl-1- hydrides, especially lithium aluminium hydride, are butene in 140 ml of toluene was heated in the presence preferred. W of 140 mg of pyridine hydrochloride with stirring and The reduction is expediently carried out in an or under a nitrogen atmosphere for 45 minutes to 120°C, ganic solvent such as an ether (e.g. diethyl ether, di a mixture of methanol and toluene being slowly dis oxan or tetrahydrofuran). tilled off azeotropically. After cooling, the residue was It is advisable to carry out the reduction at a low washed with water, dried over anhydrous sodium sul temperature, that is to say at a temperature below room. phate and concentrated. The crude product (12.2 g) temperature (e.g. at 0°C). was purified by chromatography on 250 g of silicagel. The ketones of formula IV are also novel and form Using hexane/ether (95:5) there were eluted 4.9 g of part of the present invention. They can be prepared, 25 pure trans-2,6-dimethyl-10-methylene-dodeca-1,6, 11 also in accordance with the present invention, by the trien-3-one; boiling point 0.01 = 55-65°C; UV (etha acid-catalysed reaction of a vinyl carbinol of the gen nol): A F 220 nm (e F 23,000). eral formula This ketone can also be prepared as follows: HCeC(CH)-CHOH-CH-A V b. A solution of 10 g of 2-methyl-6-methylene-octa 30 1,7-dien-3-ol and 20 g of a mixture of 3,3-dimethoxy-2- wherein A has the significance, given earlier, with an methyl-1-butene and 2-methoxy-3-methyl-butadiene enol ether of the general formula (1:1) in 100 ml of toluene was heated in the presence of 300 mg of potassium hydrogen sulphate with stirring H.C=C(CH,)-C(OR')=CH, V 35 and under an argon atmosphere for 30 minutes to 70°C and for 90 minutes to 100°-104°C, a mixture of metha wherein R represents a lower alkyl group, or a corre nol and toluene being slowly distilled off azeotropi sponding ketal of the general formula cally.
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