Process for preparing beta-santalol from 3-methylnorcamphor
    1.
    发明授权
    Process for preparing beta-santalol from 3-methylnorcamphor 失效
    从3-甲基喹啉制备苯三酚的方法

    公开(公告)号:US3662008A

    公开(公告)日:1972-05-09

    申请号:US3662008D

    申请日:1969-05-21

    申请人: PROCTER & GAMBLE

    摘要: A PROCESS FOR PREPARING B-SANTALOL, USEFUL IN PERFUME COMPOSITIONS, FROM 3-METHYLNORCAMPHOR COMPRISING THE STEPS OF (1) ALKYLATING 3-METHYLNORCAMPHOR IN STRONG BASE WITH AN ALLYL HALIDE; (2) REACTING THE REACTION PRODUCT OF STEP (1) WITH A METHYLMETALLIC COMPOUND, SUCH AS METHYLITHIUM, FOLLOWED BY HYDROLYSIS; (3) BROMINATING THE REACTION PRODUCT OF STEP (2); (4) DEHYDROBROMINATING THE REACTION PRODUCT OF STEP (3) WITH A BASE, SUCH AS SODIUM AMIDE; (5) DEHYDRATING THE REACTION PRODUCT OF STEP (4) WITH A DEHYDRATING AGENT, SUCH AS THIONYL CHLORIDE; (6) REACTING THE REACTION PRODUCT OF STEP (5) WITH A COMPOUND, SUCH AS DI(SEC.-ISO-AMYL) BORANE FOLLOWED BY AN OXIDATION; (7) REACTING THE REACTION PRODUCT OF STEP (6) WITH (CARBETHOXYETHYLIDENE)TRIPHENYLPHOSPHORANE; AND (8) REDUCING THE REACTION PRODUCT OF STEP (7) WITH A REDUCING AGENT, SUCH AS LITHIUM ALUMINUM HYDRIDE, TO OBTAIN B-SANTALOL, AND NOVEL COMPOUNDS PRODUCED THEREIN ARE DISCLOSED.

    Perfume compounds and process for preparing same
    3.
    发明授权
    Perfume compounds and process for preparing same 失效
    PERFUME化合物及其制备方法

    公开(公告)号:US3673261A

    公开(公告)日:1972-06-27

    申请号:US3673261D

    申请日:1969-12-12

    申请人: PROCTER & GAMBLE

    摘要: The compounds 2-methylene-3-exo(trans-4''-methyl-5''-hydroxypent3'' -enyl)bicyclo(2.2.1)heptane, 2-methylene-3-exo-(cis-4''-methyl5''-hydroxypent-3''-enyl)bicyclo(2.2.1)heptane and 2-methylene-3exo(4''-methyl-5''-hydroxypentyl)bicyclo(2.2.1)-heptane, all of which are useful as perfumes, and processes for their preparation are disclosed.

    摘要翻译: 化合物2-亚甲基-3-外(反式-4'-甲基-5'-羟基-3'-烯基)双环[2.2.1]庚烷,2-亚甲基-3-外 - (顺式-4'-甲基 -5'-羟基-3'-烯基)双环[2.2.1]庚烷和2-亚甲基-3-外型(4'-甲基-5'-羟基戊基)双环[2.2.1] - 庚烷,它们都是 可用作香料,以及其制备方法。

    Perfume composition including tetrahydropyranyl ether of 3-endo-methyl-3 - exo(4' - methyl - 5 - hydroxypentyl)norcamphor
    6.
    发明授权
    Perfume composition including tetrahydropyranyl ether of 3-endo-methyl-3 - exo(4' - methyl - 5 - hydroxypentyl)norcamphor 失效
    包括三烯丙基三(3-甲氧基-3-羟基戊基)异恶唑酮的四烯丙基醚的香料组合物

    公开(公告)号:US3644505A

    公开(公告)日:1972-02-22

    申请号:US3644505D

    申请日:1970-04-06

    申请人: PROCTER & GAMBLE

    IPC分类号: C07D309/12 C11B9/00 C11D1/00

    摘要: THE NOVEL ODORANT COMPOUNDS 2-METHYL-5-BROMOPENTYL TETRAHYDROPRANYL ETHER AND TERTRAHYDROPYRANYL ETHER OF 3 - ENDO - METHYL-3-EXO-(4''-METHYL-5''-HYDROXYPENTYL) PENTYL) NORCAMPHOR AND A PROCESS FOR PREPARING 2-METRHYL5-BROMOPENTYL TETRAHYDROPYRANYL ETHER, TETRAHYDROPYRANYL ETHER OF 3-ENDO-METHYL-3-EXO-(4''-METHYL-5''-HYDROXYPENTYL) NORCAMPHOR AND 3 - ENDO-METHYL-3-OX-(4''-MERHYL-5-HYDROXPENTYL) NORCAMPHOR COMPRISING THE STEPS OF: (1) THE ESTER N THE PRESENCE OF A FREE RADICAL CATALYST; (3) REDUCING THE HYDROBROMINATED ESTER TO 2-METHYL-5-BROMOPENTANOL; (4) ETHERFYING 2-METHYL-5BROMOPHENTANOL WITH DIHYDROYRAN TO OBTAIN THE NOVEL COMPOUND 2-METHYL-5BROMOPENTYL TETRAHYDROPYRANYL ETHER; (5) ALKYLATING 3METHLONOCRAMPHOR WITH THE 2 - METHY -5-BROMOPENTYL TETRAHYDROPYRANYL ETHER TO OBTAIN THE NOVEL COMPOUND, TERAHYDROPYRANYL ETHER OF 3 - ENDO - METHYL - 3-OXO(4'' METHYL -5''-HYDROXYPENTYL) NORCAMPHOR; AND (6) TREATING TERTRAHYDROPYRANYL ETHER OF 3 - ENDO - METHYL - 3-OXO(4'' METHYL - 5'' - HYDROXYPENTYL) NORCAMPHOR WITH P-TOLUENESULFONIC ACID OR HYDROCHLORID ACID TO OBTAIN 3-ENDO-METHYL3-EXCO(4''MEHYL-5''-HYDROXPENTYL) NORCAMPHOR.

    3-endo-methyl - 3 - exo(4' - methyl - 5' - hydroxypentyl) norcamphor and 2-methyl-5-bromopentanol,and process for the preparation of these compounds
    7.
    发明授权
    3-endo-methyl - 3 - exo(4' - methyl - 5' - hydroxypentyl) norcamphor and 2-methyl-5-bromopentanol,and process for the preparation of these compounds 失效
    3-内 - 甲基-3-EXO(4'-甲基-5'-羟基戊酸)异头物和2-甲基-5-溴代戊醇,以及制备这些化合物的方法

    公开(公告)号:US3579479A

    公开(公告)日:1971-05-18

    申请号:US3579479D

    申请日:1968-03-29

    申请人: PROCTER & GAMBLE

    摘要: THE NOVEL COMPOUNDS, 2-METHYL-5-BROMOPENTANOL AND 3-ENDO-METHYL-3-EXO(4'' - METHYL - 5'' - HYDROXYPENTYL) NORCAMPHOR AND THE PROCESS FOR PREPARING 2-METHYL-5BROMOPENTANOL AND 3 - ENDO-METHYL-3-EXO(4''-METHYL-5''HYDROXYPENTYL)NORCAMPHOR FROM 2 - METHYL-4-PENTENOL COMPRISING THE STEPS OF (1) BORATING 2-METHYL-4-PENTENOL WITH BORIC ACID AND/OR BORIC ANHYDRIDE TO OBTAIN TRI(2-METHYL-4-PENTENYL)BORATE; (2) HYDROBROMINATING THE TRI(2-METHYL-4-PENTENYL)BORATE IN THE PRESENCE OF A FREE RADICAL CATALYST AND, SUBSEQUENTLY, HYDROLYZING THE REACTION PRODUCT TO OBTAIN 2-METHYL-5-BROMOPENTANOL; (3) BORATING THE 2-METHYL-5-BROMOPENTANOL WITH BORIC ACID AND/OR BORIC ANHYDRIDE TO OBTAIN TRI(2-METHYL-5-BROMOPENTYL)BORATE; (4) ALKYLATING 3- METHYLNORCAMPHOR WITH THE TRI(2-METHYL-5-BROMOPENTYL)BORATE AND, SUBSEQUENTLY, HYDROLYZING THE REACTION PRODUCT TO OBTAIN 3-ENDOMETHYL-3-EXO(4''METHYL-5''-HYDROXPENTYL)NORCAMPHOR.

    Process for preparing {62 -santalol from 3-methylnorcamphor
    10.
    发明授权
    Process for preparing {62 -santalol from 3-methylnorcamphor 失效
    从3-甲基甘氨酸制备{62-安非他酮的方法

    公开(公告)号:US3679756A

    公开(公告)日:1972-07-25

    申请号:US3679756D

    申请日:1969-05-21

    申请人: PROCTER & GAMBLE

    摘要: A process for preparing Beta -santalol, useful in perfume compositions, from 3-methylnorcamphor comprising the steps of 1. ALKYLATING 3-METHYLNORCAMPHOR WITH Beta BROMOPROPIONALDEHYDE ETHYLENE GLYCOL ACETAL; 2. REACTING THE REACTION PRODUCT OF Step (1) with a methylmetallic compound, such as methyllithium, followed by acid hydrolysis; 3. REACTING THE REACTION PRODUCT OF Step (2) with (carbethoxyethylidene)triphenylphosphorane; 4. DEHYDRATING THE REACTION PRODUCT OF Step (3) with a dehydrating agent, such as thionyl chloride; and 5. REDUCING THE REACTION PRODUCT OF Step (4) with a reducing agent, such as lithium aluminum hydride, to obtain Beta santalol, AND NOVEL COMPOUNDS PRODUCED THEREIN ARE DISCLOSED.

    摘要翻译: 一种可用于3-甲基樟脑香精组合物的β-檀香醇的方法,其包括以下步骤:用β-溴代戊二醛乙二醇乙酸乙酯将3-甲基吗啉加成; 2.用甲基金属化合物如甲基锂反应步骤(1)的反应产物,然后酸解; 3.用(乙酯基亚乙基)三苯基正膦反应步骤(2)的反应产物; 4.用脱水剂如亚硫酰氯脱水步骤(3)的反应产物; 和5.用还原剂如氢化铝锂还原步骤(4)的反应产物,以获得β-檀香醇,并且公开生产的新型化合物。