Microwave induced process for the preparation of substituted 4-vinylphenols
    1.
    发明授权
    Microwave induced process for the preparation of substituted 4-vinylphenols 失效
    用于制备取代的4-乙烯基苯酚的微波诱导方法

    公开(公告)号:US06989467B2

    公开(公告)日:2006-01-24

    申请号:US10383253

    申请日:2003-03-07

    IPC分类号: C07C39/06

    摘要: The present invention relates to “a microwave induced process for the preparation of 4-vinylphenols or its derivatives” in which commercially important FEMA GRAS approved perfumery and flavouring vinylphenols (i.e. hydroxystyrenes) namely 4-vinylguaiacol (FEMA GRAS No. 2675) and 4-vinylphenol (FEMA GRAS No. 3739) as well as other useful vinylphenols such as 2,6-dimethoxy-4-vinylphenol, 2-hydroxy-4-vinylphenol, 3-hydroxy-4-vinylphenol etc. by condensation of malonic acid and 4-hydroxyphenylaldehydes or its derivatives.

    摘要翻译: 本发明涉及“微波诱导的4-乙烯基苯酚或其衍生物的制备方法”,其中商业上重要的FEMA GRAS批准了香料和调味乙烯基苯酚(即羟基苯乙烯),即4-乙烯基愈创木酚(FEMA GRAS No.2675)和4- 乙烯基苯酚(FEMA GRAS No.3739)以及其它有用的乙烯基苯酚如2,6-二甲氧基-4-乙烯基苯酚,2-羟基-4-乙烯基苯酚,3-羟基-4-乙烯基苯酚等,通过丙二酸和4 - 羟基苯基醛或其衍生物。

    Method for producing chiral dihydrotagetone, and its conversion to chiral 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone
    2.
    发明授权
    Method for producing chiral dihydrotagetone, and its conversion to chiral 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone 失效
    制备手性二氢吉他酮的方法及其转化为手性5-异丁基-3-甲基-4,5-二氢-2(3H) - 呋喃酮

    公开(公告)号:US06579992B2

    公开(公告)日:2003-06-17

    申请号:US09815335

    申请日:2001-03-23

    IPC分类号: C07D40700

    CPC分类号: C07C51/29 C07C59/347

    摘要: A natural inexpensive acyclic monoterpene ketone (dihydrotagetone) of formula (4), isolated from the oil of Tagetes sp., was smoothly oxidized with meta-periodate/potassium permanganate into 2,6-dimethyl-4-oxo-heptanoic acid of formula (3), the reduction of 3 with metal hydride such as sodium borohydride or lithium aluminium hydride provided 4-hydroxyacid of formula (2) which on without isolation undergone lactonization in acidic medium furnished two chiral centered 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone of formula (1) as an analogue of whisky lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1a) responsible for high quality of alcoholic beverage (whisky, wine, brandy and scotch), in addition, coconut flavored 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1) is also as an analogue of coconut aldehyde (&ggr;-nonalactone, F.E.M.A. No. 2751) of formula (1b) which is responsible for flavoring a wide range of food stuffs including baked goods and confectionery.

    摘要翻译: 从Tagetes sp。油中分离得到的式(4)的天然廉价的无环单萜酮(二氢t酮)用高碘酸钾/高锰酸钾被平滑地氧化成式(4)的2,6-二甲基-4-氧代 - 庚酸 3)中,用金属氢化物如硼氢化钠或氢化铝锂还原3,得到式(2)的4-羟基酸,其在酸性介质中经过内酯化而没有分离,提供了两个手性中心的5-异丁基-3-甲基-4- (1)的5-二氢-2(3H) - 呋喃酮作为负责高品质的式(1a)的威士忌内酯5-丁基-4-甲基-4,5-二氢-2(3H) - 呋喃酮的类似物 的酒精饮料(威士忌,葡萄酒,白兰地和苏格兰威士忌),此外,式(1)的椰子风味的5-丁基-4-甲基-4,5-二氢-2(3H) - 呋喃酮也是椰子的类似物 式(1b)的醛(γ-非内酯,FEMA No.2751),其负责调味各种食品,包括烘焙食品和糖果 y。

    Process for the preparation of substituted trans-cinnamaldehyde, a natural yellow dye, from phenylpropane derivatives
    4.
    发明授权
    Process for the preparation of substituted trans-cinnamaldehyde, a natural yellow dye, from phenylpropane derivatives 失效
    由苯基丙烷衍生物制备取代的反式肉桂醛(天然黄色染料)的方法

    公开(公告)号:US06566557B2

    公开(公告)日:2003-05-20

    申请号:US09805832

    申请日:2001-03-14

    IPC分类号: C07C4528

    摘要: The present invention relates to the preparation of substituted trans-cinnamaldehyde, a natural yellow dye from Phenylpropane derivatives having R2—R3—R4—R5—R6 substitution, wherein R2 to R6 equal or different, being hydrogen or hydroxy or acyl or halogen or alkyl or heterocyclic or aryl or dioxymethylene or alkoxy groups, etc., by oxidizing the said phenylpropane derivatives using a oxidising agent such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or p-chloranil or pyridinium chlorochromate (PCC) or tBuOOH or CrO3 with a catalytic amount of inorganic/organic acid or alumina, celite, and silica gel as a solid support for microwave irradiation and thus substituted trans-cinnamaldehydes, a natural yellow dye, are obtained in high yield ranging from 68-82%.

    摘要翻译: 本发明涉及取代的反式肉桂醛的制备,其是具有R2-R3-R4-R5-R6取代基的苯基丙烷衍生物的天然黄色染料,其中R2至R6相同或不同,为氢或羟基或酰基或卤素或烷基 或杂环或芳基或二氧亚甲基或烷氧基等,通过使用氧化剂如2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)或对氯醌来氧化所述苯基丙烷衍生物或 使用催化量的无机/有机酸或氧化铝,硅藻土和硅胶的氯铬酸吡啶鎓(PCC)或tBuOOH或CrO 3作为微波照射的固体支持物,从而以高产率获得取代的反式肉桂醛(天然黄色染料) 从68-82%。

    Heptanonic acid and furanone compounds and compositions
    6.
    发明授权
    Heptanonic acid and furanone compounds and compositions 失效
    庚酸和呋喃酮化合物和组合物

    公开(公告)号:US06833475B2

    公开(公告)日:2004-12-21

    申请号:US10449098

    申请日:2003-06-02

    IPC分类号: C07C59147

    CPC分类号: C07C51/29 C07C59/347

    摘要: A natural inexpensive acyclic monoterpene ketone (dihydrotagetone) of formula (4), isolated from the oil of Tagetes sp., was smoothly oxidized with meta-periodate/potassium permanganate into 2,6-dimethyl-4-oxo-heptanoic acid of formula (3), the reduction of 3 with metal hydride such as sodium borohydride or lithium aluminium hydride provided 4-hydroxyacid of formula (2) which on without isolation undergone lactonisation in acidic medium furnished two chiral centered 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone of formula (1) as an analogue of whisky lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1a) responsible for high quality of alcoholic beverage (whisky, wine, brandy and scotch), in addition, coconut flavoured 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1) is also as an analogue of coconut aldehyde (&ggr;-nonalactone, F.E.M.A. No. 2751) of formula (1b) which is responsible for flavouring a wide range of food stuffs including baked goods and confectionery.

    摘要翻译: 从Tagetes sp。油中分离得到的式(4)的天然廉价的无环单萜酮(二氢t酮)用高碘酸钾/高锰酸钾被平滑地氧化成式(4)的2,6-二甲基-4-氧代 - 庚酸 3)中,用金属氢化物如硼氢化钠或氢化铝锂还原3,得到式(2)的4-羟基酸,其在酸性介质中经过内酯化而没有分离,提供了两个手性中心的5-异丁基-3-甲基-4- (1)的5-二氢-2(3H) - 呋喃酮作为负责高品质的式(1a)的威士忌内酯5-丁基-4-甲基-4,5-二氢-2(3H) - 呋喃酮的类似物 的酒精饮料(威士忌,葡萄酒,白兰地和苏格兰威士忌),此外,式(1)的椰子风味的5-丁基-4-甲基-4,5-二氢-2(3H) - 呋喃酮也是椰子的类似物 式(1b)的醛(γ-非内酯,FEMA No.2751),其负责调味各种食品,包括烘焙食品和糖果 ery。

    Process for the preparation of pharmacologically active &agr;-asarone from toxic &bgr;-asarone rich acorus calamus oil
    7.
    发明授权
    Process for the preparation of pharmacologically active &agr;-asarone from toxic &bgr;-asarone rich acorus calamus oil 失效
    从有毒的β-asarone丰富的acorus菖蒲油制备药理学活性的α-asarone的方法

    公开(公告)号:US06590127B1

    公开(公告)日:2003-07-08

    申请号:US10107844

    申请日:2002-03-28

    IPC分类号: C07C4500

    摘要: The present invention relates to a process for the preparation of high purity and yield &agr;-asarone, trans 2,4,5-trimethoxy cinnamaldehyde, 2,4,5-trimethoxy-phenyl propionone, from &bgr;-asarone or &bgr;-asarone rich Acorus calamus oil containing &agr; and &ggr;-asarone by hydrogenating, followed by treatment with DDQ with or without solid support of silica gel or alumina in dry organic solvent and &agr;-asarone can also be obtained by treating the hydrogenated product of &bgr;-asarone or &bgr;-asarone rich Acorus calamus with DDQ in an aqueous organic solvent to obtain an intermediate 2,4,5-trimethoxy phenyl propionone, which in turn is reduced with sodiumborohydride to obtain the corresponding 2,4,5-trimethoxy-phenyl propanol and followed by final treatment with a dehydrating agent.

    摘要翻译: 本发明涉及一种制备高纯度和产率的α-雄酮,反式2,4,5-三甲氧基肉桂醛,2,4,5-三甲氧基苯丙素,由β-分析酮或富含β-福音的Acorus 通过氢化含有α和γ-胂醛的菖蒲油,然后用干燥有机溶剂和α-胂酮中的硅胶或氧化铝固体支持的DDQ进行处理,也可以通过将β-胂醛或β- 在含水有机溶剂中含有DDQ的asarone丰富的Acorus calamus,得到中间体2,4,5-三甲氧基苯丙酮,然后用硼氢化钠还原,得到相应的2,4,5-三甲氧基 - 苯基丙醇, 用脱水剂处理。