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    • 1. 发明授权
    • Process for the preparation of acyl cyanide compounds
    • 酰基氰化合物的制备方法
    • US4360479A
    • 1982-11-23
    • US276774
    • 1981-06-24
    • Kurt FindeisenHans KratzerManfred Lenthe
    • Kurt FindeisenHans KratzerManfred Lenthe
    • C07C255/17C07C51/08C07C67/00C07C253/00C07C255/40C07C255/56C07D253/06C07D253/07C07C51/083
    • C07D253/07C07C255/00
    • This invention relates to a new process for the preparation of acyl cyanides of the general formulaR.sup.1 --CO--CN (I)wherein R.sup.1 is an optionally substituted alkyl radical up to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring, which process comprises reacting a carboxylic acid anhydride of the formulaR.sup.1 --CO--O--CO--R.sup.1 (II)with an alpha-hydroxynitrile of the formula ##STR1## in which R.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom, an optionally substituted alkyl radical with 1 to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring. The acyl cyanides (I) are known compounds and can be used as starting material for the synthesis of herbicides.
    • 本发明涉及用于制备通式为R 1 -CO-CN(I)的酰基氰的新方法,其中R 1为任选取代的至多18个碳原子的烷基,具有3至12个碳原子的任选取代的环烷基 ,任选取代的芳基或任选取代的5-或6-元杂环基,其还可以与苯环稠合,该方法包括使式R 1 -CO-O-CO-R 1的羧酸酐 (II)与式(III)的α-羟基腈,其中R 2和R 3相同或不同并且表示氢原子,任选取代的具有1至18个碳原子的烷基,任选取代的环烷基与 3至12个碳原子,任选取代的芳基或任选取代的5或6元杂环基,其还可以与苯环稠合。 酰基氰化物(I)是已知的化合物,可用作合成除草剂的原料。
    • 4. 发明授权
    • Preparation of certain 2-methyl-2,3-dihydro-benzofuran-7-ols
    • 某些2-甲基-2,3-二氢 - 苯并呋喃-7-醇的制备
    • US4321204A
    • 1982-03-23
    • US170443
    • 1980-07-21
    • Gerhard ButtnerKarl-Friedrich ChristmannManfred LentheUdo Allenbach
    • Gerhard ButtnerKarl-Friedrich ChristmannManfred LentheUdo Allenbach
    • C07C41/16C07B61/00C07C41/00C07C43/23C07C67/00C07D307/86
    • C07C43/23C07D307/86
    • In the preparation of a 7-hydroxycoumaran of the formula ##STR1## in which Z is a hydrogen atom or a substituent which is inert under the subsequent reaction conditions,R.sup.1 is a hydrogen atom or a C.sub.1 to C.sub.4 -alkyl radical, andn is 1, 2 or 3wherein a pyrocatechol of the formula ##STR2## is reacted with an allyl compound of the formula ##STR3## in which Y is a halogen atom, a C.sub.1 to C.sub.4 -alkyl-sulphonate radical or an aryl-sulphonate radical,to form the mono-ether of the pyrocatechol in a first stage, and in a second stage, of the pyrocatechol monoether formed in the first stage is rearranged to a 3-alkenylpyrocatechol, and in a third stage the 3-alkenylpyrocatechol formed in the second stage, is cyclized, the improvement which comprises stages. (b) carrying out the second stage at a pH of about 2-8. Advantageously glycol monomethyl ether is employed as the solvent in all stages and the third stage is carried out with a residence time of about 1-30 minutes and with a narrow residence time spectrum corresponding to a Bodenstein-index 5, optionally in the presence of an iron salt.
    • 在制备其中Z为氢原子的式“IMAGE”的7-羟基香豆素或在随后的反应条件下为惰性的取代基时,R 1为氢原子或C 1至C 4 - 烷基,n为 1,2或3其中式IMAMA的邻苯二酚与其中Y是卤素原子,C1-C4烷基磺酸根基或芳基 - 磺酸根基团的式“IMAGE”的烯丙基化合物反应, 在第一阶段中形成邻苯二酚的单醚,在第二阶段将第一阶段中形成的邻苯二酚单醚重新排列为3-链烯基邻苯二酚,第三阶段中形成的3-链烯基邻苯二酚 阶段,循环,改进包括阶段。 (b)在约2-8的pH下进行第二阶段。 在所有阶段中,优选使用二醇单甲醚作为溶剂,第三阶段以约1-30分钟的停留时间和对应于博登斯坦指数5的窄停留时间光谱进行,任选地在 铁盐
    • 6. 发明授权
    • Process for the preparation of
2-(4-chlorophenylethyl)-2-tert.-butyl-oxirane
    • 2-(4-氯苯乙基)-2-叔丁基 - 环氧乙烷的制备方法
    • US4988829A
    • 1991-01-29
    • US373770
    • 1989-06-30
    • Paul FiedlerMartin LittmannManfred LentheAchim NoakGerd Siekmann
    • Paul FiedlerMartin LittmannManfred LentheAchim NoakGerd Siekmann
    • C07D303/08
    • C07D303/08
    • A process for making the known fungicide intermediate 2-(4-chlorophenyl ethyl)-2-tert.-butyloxirane of the formula ##STR1## comprising (a) mixing a solution of trimethylsulphonium bromide of the formula(CH.sub.3).sub.3 S.sup..sym. Br.sup..crclbar. (II) in a methanol/toluene mixture with preheated toluene and simultaneously distilling off a methanol/toluene mixture at a temperature between 65.degree. and 110.degree. C. until a suspension having a solids content between 10 and 70% by weight is formed, and(b) reacting the suspension of trimethylsulphonium bromide in toluene thus obtained with 1-(4-chlorophenyl)-4,4-dimethylpentan-3-one of the formula ##STR2## in the presence of solid potassium hydroxide, diethylene glycol and water at a temperature between 20.degree. and 120.degree. C., the amounts of the reaction components being such that per mole of 1-(4-chlorophenyl)-4,4-dimethylpentan-3-one of the formula (III) there are presentbetween 1 and 2 moles of trimethylsulphonium bromide of the formula (II),between 2 and 3 moles of solid potassium hydroxide and alsobetween 0.1 and 10% by weight of diethylene glycol and between 0.5 and 12% by weight of water, relative to 1-(4-chlorophenyl)-4,4-dimethylpentan-3-one of the formula (III).
    • 制备已知的杀真菌剂中间体式(I)的2-(4-氯苯基乙基)-2-叔丁基环氧乙烷的方法包括(a)将式(CH3)3S的三甲基锍溴化物 +)Br( - )(II)的甲醇/甲苯混合物中,同时在65-110℃的温度下蒸馏除去甲醇/甲苯混合物,直到固体含量为10至70% ,并且(b)使由此获得的甲苯中的三甲基锍溴化物的悬浮液与式(III)的1-(4-氯苯基)-4,4-二甲基戊-3-酮在存在 固体氢氧化钾,二甘醇和水,温度在20℃至120℃之间,反应组分的量使得每摩尔1-(4-氯苯基)-4,4-二甲基戊-3-酮为 式(III)中存在1至2摩尔式(II)的三甲基锍溴化物,2至3小时 固体氢氧化钾和0.1至10重量%的二甘醇和0.5至12重量%的水相对于式(I)的1-(4-氯苯基)-4,4-二甲基戊-3-酮, (三)。
    • 9. 发明授权
    • Preparation of monoalkyl ethers of hydroxyphenols
    • 羟基苯酚的单烷基醚的制备
    • US4383126A
    • 1983-05-10
    • US315126
    • 1981-10-26
    • Gerhard ButtnerArtur JudatUdo AllenbachManfred Lenthe
    • Gerhard ButtnerArtur JudatUdo AllenbachManfred Lenthe
    • C07C41/00C07C41/16C07C43/23C07C67/00
    • C07C41/16
    • A process for the preparation of a monoalkyl ether of a hydroxyphenol of the formula ##STR1## in which Z each independently is hydrogen or a substituent which is stable under the reaction conditions,R is lower alkyl, andn is 1, 2, 3 or 4,comprising reacting a hydroxyphenol of the formula ##STR2## with an alkyl halide, alkyl sulphonate or aryl sulphonate alkylating agent of the formulaR--Xin which X is a halogen atom, or an alkylsulphonyloxy or arylsulphonyloxy radical,at a temperature from about 130.degree. C. to 200.degree. C. and in the presence of an alkali metal base or alkaline earth metal base and of a diluent comprising a polyhydroxyalkyl ether having at least one OH group. Advantageously the base is sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate, the hydroxyphenol is pyrocatechol, the alkylating agent is isopropyl chloride, isopropyl C.sub.1-4 -alkyl-1-sulphonate, isopropyl benzenesulphonate or isopropyl tolyenesulphonate, and the polyhydroxyalkyl ether is glycol monomethyl ether, about 1.5 to 1.8 mols of alkylating agent and about 1 to 2 mols of the base being employed per mol of pyrocatechol, about 1.5 to 2.5 parts by weight of the glycol monomethyl ether being employed per part by weight of pyrocatechol, the reaction being effected in an inert atmosphere under elevated pressure.
    • 制备式“IMAGE”的羟基苯酚的单烷基醚的方法,其中Z各自独立地为氢或在反应条件下稳定的取代基,R为低级烷基,n为1,2,3或 4,包括使式(ⅩⅧ)的羟基苯酚与其中X为卤素原子的式RX的烷基卤化物,烷基磺酸盐或芳基磺酸盐烷基化剂或烷基磺酰氧基或芳基磺酰氧基在约130℃ 在碱金属碱或碱土金属碱和包含具有至少一个OH基团的多羟基烷基醚的稀释剂的存在下进行。 有利地,碱是碳酸钠,碳酸氢钠,碳酸钾或碳酸氢钾,羟基苯酚是邻苯二酚,烷基化剂是异丙基氯,异丙基C 1-4 - 烷基-1-磺酸酯,异丙基苯磺酸酯或异丙基甲苯磺酸酯,多羟基烷基醚是 二醇单甲醚,约1.5-1.8摩尔烷基化剂和每摩尔邻苯二酚使用约1-2摩尔的碱,每重量份邻苯二酚使用约1.5-2.5重量份的二醇单甲醚, 反应在惰性气氛中在升高的压力下进行。
    • 10. 发明授权
    • Preparation of chlorinated N-methyl-imidazoles and N-methyl-imidazolines
    • 氯化N-甲基 - 咪唑和N-甲基 - 咪唑啉的制备
    • US4216332A
    • 1980-08-05
    • US974411
    • 1978-12-29
    • Manfred LentheGerhard Dankert
    • Manfred LentheGerhard Dankert
    • C07C67/00C07C239/00C07C241/00C07C271/00C07D233/28C07D233/68
    • C07D233/28C07D233/68
    • In the preparation of chlorinated N-methyl-imidazoles and N-methyl-imidazolines of the formula ##STR1## in which n represents the number 0, 1, 2 or 3 andm represents the number 0 or 1, a double bond being present between the C atoms in the 4-position and 5-position when m is 0, and a single bond being present when m is 1,by chlorinating N,N-dimethylaminoacetonitrile of the formula(CH.sub.3).sub.2 N--CH.sub.2 --CNor its hydrochloride, the improvement which comprises introducing aminoacetonitrile or its hydrochloride into a mixture of its chlorination products, with simultaneous addition of chlorine gas, in the absence of a solvent, at a temperature from about 70.degree. to 150.degree. C. The product can be further chlorinated at 130.degree. to 220.degree. C. to produce tetrachloro-ethylene-bis-isocyanide dichloride.
    • 在制备式“IMAGE”的氯代N-甲基 - 咪唑和N-甲基 - 咪唑啉的制备中,其中n代表数字0,1,2或3,m表示数字0或1,双键存在于 当m为0时,4位和5位的C原子,当m为1时存在单键,通过氯化式(CH3)2N-CH2-CN或其盐酸盐的N,N-二甲基氨基乙腈, 其改进包括将氨基乙腈或其盐酸盐引入其氯化产物的混合物中,在约70-150℃的温度下,在不存在溶剂的情况下同时加入氯气。产物可以进一步在 130℃〜220℃,生成四氯 - 乙烯 - 双 - 异氰酸酯二氯化物。