The present invention relates to novel cyclopropane derivatives represented by Formula I:

##STR00001##

wherein R represents a hydrocarbon group containing 1-20 carbon atoms or an ester containing 1-20 carbon atoms;

wherein R′ represents a C.sub.1-C.sub.6 acyclic carboxylic acid ester, a C.sub.4-C.sub.6 cyclic carboxylic acid ester or —OR″, and R″ is selected from the group consisting of H, a C.sub.1-C.sub.6 acyclic hydrocarbon group, a C.sub.3-C.sub.6 carbocyclic ring and a C.sub.4-C.sub.5 heterocyclic ring; and

wherein the composition is selected from the group consisting of a flavor composition and a fragrance composition.

The invention provides a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat or light, a high clearing point (or a high maximum temperature), a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a small dielectric anisotropy, a suitable elastic constant and a good compatibility with other liquid crystal compounds, a liquid crystal composition including this compound, and a liquid crystal display device containing this composition. The invention provdes a compound represented by formula (1):

##STR00001##

where R.sup.1 and R.sup.2 is alkyl having 1 to 20 carbons or the like; one of L.sup.1 and L.sup.2 is both hydrogens, and the other is both fluorines; Z.sup.1 and Z.sup.2 are independently a single bond, —COO—, —OCO—, —OCH.sub.2—, —CH.sub.2O—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2CH.sub.2—, —CH═CH—, —C≡C— or the like.

The invention provides a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat or light, a high clearing point (or a high maximum temperature), a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a small dielectric anisotropy, a suitable elastic constant and a good compatibility with other liquid crystal compounds, a liquid crystal composition including this compound, and a liquid crystal display device containing this composition. The invention provdes a compound represented by formula (1):

##STR00001##

where R.sup.1 and R.sup.2 is alkyl having 1 to 20 carbons or the like; one of L.sup.1 and L.sup.2 is both hydrogens, and the other is both fluorines; Z.sup.1 and Z.sup.2 are independently a single bond, —COO—, —OCO—, —OCH.sub.2—, —CH.sub.2O—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2CH.sub.2—, —CH═CH—, —C≡C— or the like.

This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M.sup.m+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R.sup.10a, R.sup.10b, R.sup.10c, R.sup.10d, R.sup.10a′, R.sup.10b′, R.sup.10c′, R.sup.10d′, Z and Z′ have the meanings as defined in the description.

This invention relates to a process for the synthesis of a non-racemic cyclohexene compound of formula (I) by a Diels-Alder reaction of a compound of formula (II) with a compound of formula (III) wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and Y have the meanings as defined in the description in the presence of a catalyst comprising at least one m-valent metal cation M.sup.m+ wherein the metal M is selected from Scandium (Sc), Yttrium (Y), Lanthanum (La), Cerium (Ce), Praseodymium (Pr), Neodymium (Nd), Promethium (Pm), Samarium (Sm), Europium (Eu), Gadolinium 15 (Gd), Terbium (Tb), Dysprosium (Dy), Holmium (Ho), Erbium (Er), Thulium (Tm), Ytterbium (Yb), Lutetium (Lu), Gallium (Ga) and Indium (In), and m is an integer of 1, 2 or 3, and a chiral ligand of the formula (IV) wherein R.sup.10a, R.sup.10b, R.sup.10c, R.sup.10d, R.sup.10a′, R.sup.10b′, R.sup.10c′, R.sup.10d′, Z and Z′ have the meanings as defined in the description.

A compound having a group represented by formula (Ia): ##STR00001##
wherein R.sup.1 and R.sup.2 each independently represent a C.sub.1 to C.sub.8 fluorinated alkyl group, ring W represents a C.sub.5 to C.sub.18 alicyclic hydrocarbon group that may have a substituent, and * represents a binding site.

A compound having a group represented by formula (Ia): ##STR00001##
wherein R.sup.1 and R.sup.2 each independently represent a C.sub.1 to C.sub.8 fluorinated alkyl group, ring W represents a C.sub.5 to C.sub.18 alicyclic hydrocarbon group that may have a substituent, and * represents a binding site.

The present invention has an object of providing a carboxylate compound that is useful as a raw material for fragrance compositions and has a fruity aroma, a method for producing the same, and a fragrance composition containing the carboxylate compound.

The carboxylate compound of the present invention is represented by Formula (1).

##STR00001## where, R is an alkyl group having from 2 to 6 carbons.

The present invention has an object of providing a carboxylate compound that is useful as a raw material for fragrance compositions and has a fruity aroma, a method for producing the same, and a fragrance composition containing the carboxylate compound.

The carboxylate compound of the present invention is represented by Formula (1).

##STR00001## where, R is an alkyl group having from 2 to 6 carbons.

Process for hydrogenating aromatic compounds over a solid catalyst in the presence of a hydrogen-containing gas comprising a first reactor operated in loop mode, a second reactor operated in straight pass, at least part of the output of the first reactor is supplied to the second reactor, characterized in that the first reactor is configured as a trickle bed reactor and is operated in trickle bed mode and the second reactor is operated such that the catalyst present therein is partially flooded.