The present invention relates to a process for preparing a haloalkyl alkoxymethyl ether compound of the following general formula (1), wherein X.sup.1 represents a halogen atom, R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and n represents an integer of 2 to 7, the process comprising the steps of converting a haloalkyl alkoxymethyl ether compound of the following general formula (1) into a nucleophilic reagent, (2n+2)-alkoxymethoxyalkyl compound, of the following general formula (2), wherein M.sup.1 represents Li, MgZ.sup.1, CuZ.sup.1, or CuLiZ.sup.1, Z.sup.1 represents a halogen atom or Z.sup.2, subsequently subjecting the nucleophilic reagent, (2n+2)-alkoxymethoxyalkyl compound (2), to a nucleophilic addition reaction with propylene oxide of the following formula (3), to obtain a hydroxyalkyl alkoxymethyl ether compound of the following general formula (4), and subjecting the hydroxyalkyl alkoxymethyl ether compound (4) to a halogenation reaction to obtain the aforesaid haloalkyl alkoxymethyl ether compound (1).

##STR00001##

The present invention relates to a process for preparing a haloalkyl alkoxymethyl ether compound (1B), wherein X.sup.1 represents a halogen atom, and R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, the process comprising the steps of converting a haloalkyl alkoxymethyl ether compound of the following general formula (1A), wherein X.sup.1 and R.sup.1 are as defined above, into a nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl, of the following general formula (2A), wherein M.sup.1A represents Li, MgZ.sup.1A, CuZ.sup.1A, or CuLiZ.sup.1A, Z.sup.1A represents a halogen atom or a 4-alkoxymethoxy-1-methylbutyl group, and R.sup.1 is as defined above, and subsequently subjecting the nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl (2A), to a nucleophilic addition reaction with propylene oxide of the following formula (3) to obtain 6-hydroxy-4-methylheptyl alkoxymethyl ether compound of the following general formula (4), wherein R.sup.1 is as defined above, and subjecting the 6-hydroxy-4-methylheptyl alkoxymethyl ether compound (4) to a halogenation reaction to form the aforesaid haloalkyl alkoxymethyl ether compound (1B).

##STR00001##

The present invention relates to a process for preparing a haloalkyl alkoxymethyl ether compound (1B), wherein X.sup.1 represents a halogen atom, and R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, the process comprising the steps of converting a haloalkyl alkoxymethyl ether compound of the following general formula (1A), wherein X.sup.1 and R.sup.1 are as defined above, into a nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl, of the following general formula (2A), wherein M.sup.1A represents Li, MgZ.sup.1A, CuZ.sup.1A, or CuLiZ.sup.1A, Z.sup.1A represents a halogen atom or a 4-alkoxymethoxy-1-methylbutyl group, and R.sup.1 is as defined above, and subsequently subjecting the nucleophilic reagent, 4-alkoxymethoxy-1-methylbutyl (2A), to a nucleophilic addition reaction with propylene oxide of the following formula (3) to obtain 6-hydroxy-4-methylheptyl alkoxymethyl ether compound of the following general formula (4), wherein R.sup.1 is as defined above, and subjecting the 6-hydroxy-4-methylheptyl alkoxymethyl ether compound (4) to a halogenation reaction to form the aforesaid haloalkyl alkoxymethyl ether compound (1B).

##STR00001##

The present invention relates to an n-heterocyclic carbene (NHC) type palladium catalyst and its preparation method as well as applications. Its preparation process is as below: select glyoxal as the raw material to synthesize glyoxaldiimine in the presence of Lewis acid or Bronsted acid, and then react with paraformaldehyde to get the NHC type ligand. Use palladium.sup.(II) to react with the compound containing carbon-nitrogen double bonds to get palladium.sup.(II) cyclic dimer; make the palladium cyclic dimer and the NHC type ligand coordinated to get the NHC type palladium catalyst. The palladium catalyst with a brand new structure according to the present invention, boasts high activity and multi-purpose. In addition, it shows excellent reaction activity in a lot of catalytic-coupling reactions including Suzuki-Miyaura, Heck, Buchwald-Hartwig, Kumada-Tamao-Corriu, Sonogashira, Negishi and -ketone arylation reactions, and some reactions even can be carried out with the presence of an extremely low concentration of catalyst, exhibiting favorable industrialization prospect.

A process for the preparation of a compound of formula (V):

##STR00001## comprising at least the step of reacting a compound of formula (VI)

##STR00002## with a compound (VII)

##STR00003## wherein; R.sub.2 is hydrogen or a C1-C20 hydrocarbyl radical provided that at least one R.sub.2 is not hydrogen; R.sub.5 is hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; R.sub.6 is hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; n is 1, 2 or 3; each R.sub.8 is a C1-20 hydrocarbyl group; and Hal is a halide; in the presence of a nickel imidazolidin-2-ylidene compound.

A process for the preparation of a compound of formula (V):

##STR00001## comprising at least the step of reacting a compound of formula (VI)

##STR00002## with a compound (VII)

##STR00003## wherein; R.sub.2 is hydrogen or a C1-C20 hydrocarbyl radical provided that at least one R.sub.2 is not hydrogen; R.sub.5 is hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; R.sub.6 is hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; n is 1, 2 or 3; each R.sub.8 is a C1-20 hydrocarbyl group; and Hal is a halide; in the presence of a nickel imidazolidin-2-ylidene compound.

A catalyst in solid particulate form free from an external carrier material comprising (I) a complex of formula (I) ##STR00001## wherein M is zirconium or hafnium; each X is a sigma ligand; L is a divalent bridge selected from R.sub.2C, R.sub.2CCR.sub.2, R.sub.2Si, R.sub.2SiSiR.sub.2, R.sub.2Ge, wherein each R is independently a hydrogen atom, C1-C20-alkyl, tri(C1-C20-alkyl)silyl, C6-C20-aryl, C7-C20-arylalkyl or C7-C20-alkylaryl; each R.sub.2 is independently hydrogen or a C1-C20 hydrocarbyl radical provided that at least one R.sub.2 is not hydrogen; each R.sub.5 is independently hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; each R.sub.6 is independently hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; each n is independently 1, 2 or 3; and each R.sub.8 is a C1-20 hydrocarbyl group; and (ii) a cocatalyst comprising a compound of a group 13 metal, e.g. Al or boron.

A catalyst in solid particulate form free from an external carrier material comprising (I) a complex of formula (I) ##STR00001## wherein M is zirconium or hafnium; each X is a sigma ligand; L is a divalent bridge selected from R.sub.2C, R.sub.2CCR.sub.2, R.sub.2Si, R.sub.2SiSiR.sub.2, R.sub.2Ge, wherein each R is independently a hydrogen atom, C1-C20-alkyl, tri(C1-C20-alkyl)silyl, C6-C20-aryl, C7-C20-arylalkyl or C7-C20-alkylaryl; each R.sub.2 is independently hydrogen or a C1-C20 hydrocarbyl radical provided that at least one R.sub.2 is not hydrogen; each R.sub.5 is independently hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; each R.sub.6 is independently hydrogen or a C1-20 hydrocarbyl group optionally containing one or more heteroatoms from groups 14-16; each n is independently 1, 2 or 3; and each R.sub.8 is a C1-20 hydrocarbyl group; and (ii) a cocatalyst comprising a compound of a group 13 metal, e.g. Al or boron.

A catalyst comprising (i) an asymmetric complex of formula (I) ##STR00001## wherein M is zirconium or hafnium; each X is a sigma ligand; L is a divalent bridge selected from R.sub.2C, R.sub.2CCR.sub.2, R.sub.2Si, R.sub.2SiSiR.sub.2, R.sub.2Ge, wherein each R is independently a hydrogen atom, C1-C20-alkyl, tri(C1-C20-alkyl)silyl, C6-C20-aryl, C7-C20-arylalkyl or C7-C20-alkylaryl; R.sub.2 and R.sub.2 are each independently linear C.sub.1-10 hydrocarbyl; R.sub.5 and R.sub.5 are each independently hydrogen or a C1-20 hydrocarbyl group; R.sub.6 and R.sub.6 are each independently hydrogen or a C1-20 hydrocarbyl group; R.sub.7 is hydrogen or a C1-20 hydrocarbyl group or is ZR.sub.3; Z is O or S, preferably O; R.sub.3 is a C1-10 hydrocarbyl group; Ar is an aryl or heteroaryl group having up to 20 carbon atoms optionally substituted by one or more groups R.sub.8; Ar is an aryl or heteroaryl group having up to 20 carbon atoms optionally substituted by one or more groups R.sub.8; and R.sub.8 and R.sub.8 are each independently is a C1-20 hydrocarbyl group; with the proviso that at least one of R.sub.6 or R.sub.7 is not H; and (ii) a cocatalyst comprising a compound of a group 13 metal, e.g. boron.

Described herein are methods for making intermediates useful in the production of fragrance ingredients starting from myrcene. In particular, methods for making geranyl chloride, (E)-6,10-dimethylundeca-1,5,9-triene and (E)-6,10-dimethylundeca-5,9-dien-1-yne are described. Methods for making other intermediates in the process are also described.