Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a cyclic compound cycloalkanone used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (III), and the method includes: a step 1: reacting a compound represented by General Formula (I) and alcohol having 1 or more and 4 or less of carbon atoms in the presence of a first acid catalyst and optionally a dehydrating agent; and a step 2: reacting a crude product obtained in the step 1 and a compound represented by General Formula (II) in the presence of a second acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (III). The step 1 and the step 2 are consecutively performed. In the formulae above, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or less of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

The present disclosure is directed to 1-(4-methyl cyclohex-1-en-1-yl)ethan-1-one derivatives having unique and desired flavor and/or fragrance characteristics, as well as the synthesis and application of the derivatives. The compounds of the present disclosure can be employed alone or incorporated as fragrance or flavor ingredients to modify or enhance already existing fragrance compositions, solvents, media, and the like.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I ##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalization reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone. The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I ##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalization reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone. The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I

##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalisation reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone.

The method affords an easier and more efficient method of preparation.

A method of making spirogalbanone includes the steps of: (a) subjecting ethynylspirodecanol to a Rupe rearrangement to give a compound of the formula I

##STR00001## (b) converting the compound of (a) to a C1-C4 alkyl acetal; (c) subjecting the acetal to a trans-acetalisation reaction with allyl alcohol in the presence of a mild acid catalyst; (d) heating the product of (c) in the presence of an acid catalyst to give an allylenolether; and (e) subjecting the product of (d) to a Claisen rearrangement to give spirogalbanone.

The method affords an easier and more efficient method of preparation.