Shin-etsu Chemical Co., Ltd.

Ryo Komatsu

Takeshi Kinsho

Takeru Watanabe

Yuki Miyake

The present invention provides a process for preparing an 11-halo-3-undecene compound (7) in which Xrepresents a halogen atom, the process comprising a step of subjecting a nucleophilic reagent, 3-hexenyl compound (5): in which Mrepresents Li or MgZ, wherein Zrepresents a halogen atom or a 3-hexenyl group, to a coupling reaction with a 1-halo-5-halopentane compound (6) in which Xand Xmay be same with or different from each other and represent a halogen atom, to produce the 11-halo-3-undecene compound (7). The present invention also provides a process for preparing a 9-dodecenal compound (4): the process comprising a step of subjecting a nucleophilic reagent, 8-undecenyl compound (1) in which Mrepresents Li or MgZ, wherein Zrepresents a halogen atom or an 8-undecenyl group, and an orthoformic ester compound (2) in which R may be same with or different from each other and represents an alkyl group having 1 to 6 carbon atoms, to a nucleophilic substitution reaction to produce a 1,1-dialkoxy-9-dodecene compound (3) in which R are as defined above; and hydrolyzing the 1,1-dialkoxy-9-dodecene compound (3) thus obtained to produce the 9-dodecenal compound (4).

11-halo-3-undecene compound and a process for preparing the same and a process for preparing 9-dodecenal compound

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1).

(6Z,9Z)-6,9-dodecadien-1-yne and a process for preparing the same

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): RCHOCHOCHCHCH&#x2550;CH(CH)X(1) wherein Rrepresents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, Xrepresents a halogen atom, and 'a' represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH&#x2550;CHCH&#x2550;CH(CH)OAc (5) wherein 'a' is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH&#x2550;CHCH&#x2550;CH(CH)OH (6) wherein &#x201c;a&#x201d; is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

Haloalkenyl alkoxymethyl ether compound and a process for preparing a terminal conjugated alkadien-1-yl acetate compound and a terminal conjugated alkadien-1-ol compound therefrom

The present invention provides a process for preparing (9Z,11E)-9,11-hexadecadienal of the following formula (4), the process comprising: subjecting (2E)-2-heptenal of the following formula (1) to a Wittig reaction with a triarylphosphonium 9,9-dialkoxynonylide compound of the following general formula (2), wherein Ar represents an aryl group that may be same with or different from each other, and Rand Rrepresent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or Rand Rmay form together a divalent hydrocarbon group, R&#x2014;R, having 2 to 10 carbon atoms to form a (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound of the following general formula (3), wherein Rand Rare as defined above; and hydrolyzing the (5E,7Z)-16,16-dialkoxy-5,7-hexadecadiene compound (3) to form (9Z,11E)-9,11-hexadecadienal (4). 

Process for preparing (9Z,11E)-9,11-hexadecadienal

A process for preparing a dienynal compound of the following general formula (2):CH&#x2550;CHC&#x2261;CCH&#x2550;CH(CH)CHO&#x2003;&#x2003;(2), wherein n represents an integer of 0 to 11, the process comprising a step of hydrolyzing a dialkoxyalkadienyne compound of the following general formula (1):CH&#x2550;CHC&#x2261;CCH&#x2550;CH(CH)CH(OR)(OR)&#x2003;&#x2003;(1) wherein Rand Rrepresent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or Rand Rmay be bonded to each other to form a divalent hydrocarbon group, R-R, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2). 

Dialkoxyalkadienyne compound and a process for preparing the same and a process for preparing a dienynal compound

The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3), the process comprising at least a step of subjecting pentanoic anhydride of the following formula (1) and a 2-pentyl nucleophilic reagent of the following general formula (2), in which M represents Li, MgZ, or ZnZ, wherein Zrepresents a halogen atom or a 2-pentyl group, to a nucleophilic substitution reaction to produce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (7), the process comprising at least steps of preparing 4-methyl-5-nonanone and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (7). 

Processes for preparing 4-methyl-5-nonanone and 4-methyl-5-nonanol

One object of the invention is to provide a method for preparing a 9,9-dialkoxy-7-nonynoate ester and (7E)-7,9-decadienoate ester, which are valuable as intermediates. The method for preparing a (7E)-7,9-decadienoate ester (5) comprises at least steps of: hydrolyzing a 9,9-dialkoxy-7-nonenoate ester (2), RO(RO)CHCH&#x2550;CH(CH)COR, to form a (7E)-9-oxo-7-nonenoate ester (3); and subjecting the (7E)-9-oxo-7-nonenoate ester (3) to a Wittig reaction with a triarylphosphonium methylide (4), ArP&#x2550;CH, to form the (7E)-7,9-decadienoate ester (5). The 9,9-dialkoxy-7-nonenoate ester may be prepared by, for example, reducing a 9,9-dialkoxy-7-nonynoate ester (1). 

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Niigata, Japan

Ryo Komatsu