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United States Patent (19) 11 Patent Number: 4,659,808 Matsumura 45) Date of Patent: Apr

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United States Patent (19) 11 Patent Number: 4,659,808 Matsumura 45) Date of Patent: Apr United States Patent (19) 11 Patent Number: 4,659,808 Matsumura 45) Date of Patent: Apr. 21, 1987 (54) PROCESS FOR PRODUCING KETALS OF 3,598,804 8/1971 Hindley et al. ..................... 536/124 2-KETOGULONIC ACID OR ITS ESTERS 3,607,862 9/1971 Jaffe et al. ........................... 536/124 3,622,506 11/1971 Hindley et al. ....... ... 536/124 75) Inventor: Koichi Matsumura, Osaka, Japan 4,460,767 7/1984 Matsumura et al. .. ... 536/124 73) Assignee: Takeda Chemical Industries, Ltd., 4,464,204 8/1984 Niekamp et al...... ... 536/124 Osaka, Japan 4,464,530 8/1984 Matsumura et al. ................ 536/124 (21) Appl. No.: 654,248 FOREIGN PATENT DOCUMENTS 22 Filed: Sep. 25, 1984 00761 18 9/1982 European Pat. Off. ............ 536/124 Primary Examiner-Johnnie R. Brown (30) Foreign Application Priority Data Attorney, Agent, or Firm-Wegner & Bretschneider Sep. 28, 1983 (JP) Japan ................................ 58-181305 (57) ABSTRACT 51 Int. Cl." ............................................... CO7H 1/00 A novel process is disclosed for production of ketals of 52 U.S.C. ................................... 536/18.5; 536/120; 2-ketogulonic acid or of its esters, which comprises 536/124; 536/4.1 reacting 2-ketogulonic acid or its esters with a ketone in 58 Field of Search ....................... 536/124, 120, 18.5 the presence of a ketal formation catalyst. The process (56) References Cited is advantageous from the industrial point of view to U.S. PATENT DOCUMENTS give ketals of 2-ketogulonic acid or of its esters. 3,139,443 6/1964 Sosnovsky .......................... 536/124 13 Claims, No Drawings 4,659,808 1. 2 constituting said esters are not specifically restricted, PROCESS FOR PRODUCING KETALS OF unless they inhibit the present ketal formation reaction, 2-KETOGULONCACD OR TS ESTERS but their specific examples include alkyl, cycloalkyl, alkenyl and aralkyl groups, which each are exemplified This invention relates to a process for producing 5 by the following: ketals of 2-ketogulonic acid or of its esters. More partic As the alkyl group, there may be mentioned those ularly, the present invention is concerned with a pro having a carbon number in the range of 1 to 18, such as cess for producing 2,3:4,6-di-O-ketals or 2,3-O-ketals of methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, 2-ketogulonic acid or of its esters. t-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, 2,3:4,6-Di-O-ketals of 2-ketogulonic acid and those of O decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexa its esters, as an intermediate in the synthesis of vitamin decyl, heptadecyl and octadecyl; as the cycloalkyl C, are important as 2-ketogulonic acid and its esters T. group, by way of example, there may be mentioned C. Crawford and S. A. Crawford; Advances in Carbo cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and hydrate Chemistry and Biochemistry, vol. 37, pp. cyclooctyl; as the alkenyl group, there may be men 89-106 (1980), and U.S. Pat. No. 2,159,191 (1939). 15 tioned those having a carbon number of 3 to 14 such as 2,3-O-Ketals of 2-ketogulonic acid esters also have been 2-propenyl and 2-methyl-2-propenyl groups; and as the known to be useful not only as a synthetic intermediate aralkyl group, by way of example, there may be men in the production of vitamin C British Pat. No. 601,789 tioned groups having an aryl group substituted by alkyl and U.S. Pat. No. 2,491,933) but also as a synthetic group with a carbon number in the range of 1 to 4 (e.g., intermediate for the derivatives of vitamin C J. Kiss 20 benzyl, phenethyl, 1-phenylethyl, 1- or b 3-phenylpro and W. Arnold; Experimentia, vol. 36, pp. 1138 (1980) pyl, 1-methyl-3-phenylpropyl, 4-phenylbutyl), such aryl and J. Kiss and W. Arnold et al.; Helv. Chim. Acta, vol. groups being typified by the phenyl, furyl, thienyl and 63, pp. 1728 (1980)). pyridyl groups which may be substituted by lower alkyl 2-Ketogulonic acid or its esters, by conversion into and lower alkoxy groups, halogens, etc. their 2,3:4,6-di-O-ketals or 2,3-O-ketals, can yield the 25 2-Ketogulonic acid esters are obtained by reacting compounds which are readily soluble in organic sol 2-ketogulonic acid with an alcohol having the above vents such as benzene, toluene, acetone, dichlorometh mentioned alkyl, cycloalkyl, alkenyl or aralkyl group in ane, chloroform, ether and dioxane, and this can like the presence of an acid catalyst according to the con wise be employed as a procedure for purifying 2 ventionally known method or a method similar thereto. ketogulonic acid and its esters. 30 The ketone being usable in the present invention is Conventionally, 2,3:4,6-di-O-ketals of 2-ketogulonic not specifically restricted, but use is preferably made of acid have been synthesized by subjecting a 2,3:4,6-di-O- those having a carbon number of 3 to 7, of which spe ketal of sorbose to a reaction such as chemical oxidation cific examples include a dialkyl ketone having a carbon with potassium permanganate, sodium hypochlorite, number of 3 to 6 such as acetone, methyl ethyl ketone, etc., air oxidation with use of a platinum catalyst, etc. or 35 diethyl ketone, di-n-propyl ketone and di-i-propyl ke electrochemical oxidation T. C. Crawford and S. A. tone; and a cyclic ketone having a carbon number of 5 Crawford; Advances in Carbohydrate Chemistry and to 7 such as cyclopentanone, cyclohexanone and cyclo Biochemistry, vol. 37, pp. 93-96 (1980). 2,3:4,6-di-O- heptanone. The amount of these ketones to be used is at Isopropylidene derivatives of 2-ketogulonic acid esters least 2 to 10 times of the theoretical molar quantity, but can be produced also by air oxidation reaction of 40 it is normally advantageous to use these ketones in large 2,3:4,6-di-O-isopropylidene derivatives of sorbose in the excess as the reaction reagent and solvent. presence of alcohol (The Japanese Unexamined Patent The reaction in the production process according to Publication No. 94395/1980). the present invention is carried out in the presence of a On the other hand, 2,3-O-isopropylidene derivatives ketal formation catalyst. As the said catalyst, use can be of 2-ketogulonic acid esters have been synthesized by 45 made of any catalyst that promotes the ketal formation partial hydrolysis reaction of 2,3:4,6-di-O-isopropyli reaction, but generally, halides and other acid catalysts dene derivatives of 2-ketogulonic acid esters J. Kiss, are suitable. Specifically, there may be mentioned fluo W. Arnold, et al.; Helv. Chim. Acta, vol. 63, pp. 1728 rine-containing catalysts, chlorine-containing catalysts, (1980) or by the esterification reaction accompanied bromine-containing catalysts, iodine-containing cata with partial hydrolysis reaction of the 4,6-O-isopropyli 50 lysts, etc. as being exemplified in the following: dene group in 2,3:4,6-di-O-isopropylidene derivatives of As the fluorine-containing catalyst, there may be 2-ketogulonic acid esters British Pat. No. 601,789 and mentioned hydrogen fluoride, hydrogentetrafluorobo U.S. Pat. No. 2,491,933). rate, fluorosulfuric acid, trifluoromethanesulfonic acid, The present inventor attempted to conduct a reaction H type ion exchange resins having perfluorosulfonic of 2-ketogulonic acid or its ester with a ketone, which is 55 acid residues being typified by Nafion-HCR), perfluoro different from the above-mentioned known processes, carboxylic acids being represented by trifluoroacetic and found that said reaction in the presence of a ketal acid, acid fluorides being typified by formyl fluoride formation catalyst proceeds favorably from the indus and acetyl fluoride, sulfonyl fluorides being represented trial point of view to give a ketal of 2-ketogulonic acid by methanesulfonyl fluoride, sulfuryl fluorochloride, or of its ester, and this has culminated into the present fluorine monochloride, fluorine monobromide, fluorine invention. monoiodide, boron trifluoride, boron trifluoride.ether Thus, the present invention is directed toward a pro complex, antimony pentafluoride, molybdenum fluo cess for producing ketals of 2-ketogulonic acid or of its ride, arsenic pentafluoride, etc. esters, which comprises reacting 2-ketogulonic acid or As the chlorine-containing catalyst, there may be its ester with a ketone in the presence of a ketal forma 65 mentioned hydrogen chloride, perchloric acid, trichlo tion catalyst. roacetic acid, acid chlorides being typified by formyl In the present invention, use is made of 2-ketogulonic chloride and acetyl chloride, phosgene, thionyl chlo acid or its esters as a starting compound. The groups ride, sulfuryl chloride, sulfonyl chlorides being repre 4,659,808 3 4. sented by methanesulfonyl chloride, trimethylsilyl chlo sulfate, ammonium iron citrate, ammonium ferric oxa ride, boron trichloride, ammonium chloride, aluminum late, etc.). chloride, silicon tetrachloride, phosphorus trichloride, As the iodine-containing catalyst, use may be made of phosphorus oxychloride, phosphorus pentachloride, hydrogen iodide as such or in the form of hydriodic sulfur monochloride, sulfur dichoride, chlorine, N acid produced by dissolving hydrogen iodide in water, chlorosuccinimide, calcium chloride, titanium tetra or compounds existing in the form of hydrogen iodide chloride, ferric chloride, cupric chloride, zinc chloride, in the reaction system or systems liberating hydrogen gallium perchlorate.hydrate, germanium tetrachloride, iodide in the reaction system. zirconium tetrachloride, rhodium chloride, palladium Examples of the above-mentioned compounds exist chloride, stannic chloride, stannous chloride, antimony O ing in the form of hydrogen iodide in the reaction sys pentachloride, antimony trichloride, molybdenum pen tem or systems liberating hydrogen iodide in the reac tachloride, tantalum pentachloride, tungsten hexachlo tion system include (1) metal iodides and acids, (2) io ride, lanthanum chloride, cerium chloride, neodymium dinating agents, (3) iodinating agents and reducing chloride, erbium chloride, ytterbium chloride, and so agents and (4) Lewis acids containing iodine.
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