The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5):
CH.sub.2═CHCH═CH(CH.sub.2).sub.aCHO   (5)
wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1):
R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aCH(OR.sup.2)(OR.sup.3)   (1)
wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.2 and R.sup.3 may form together a divalent hydrocarbon group, R.sup.2-R.sup.3, having 2 to 10 carbon atoms, and “a” is as defined above.

The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5):
CH.sub.2═CHCH═CH(CH.sub.2).sub.aCHO   (5)
wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1):
R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aCH(OR.sup.2)(OR.sup.3)   (1)
wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.2 and R.sup.3 may form together a divalent hydrocarbon group, R.sup.2-R.sup.3, having 2 to 10 carbon atoms, and “a” is as defined above.

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aX.sup.1 (1) wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X.sup.1 represents 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.sub.2═CHCH═CH(CH.sub.2).sub.aOAc (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.sub.2═CHCH═CH(CH.sub.2).sub.aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5):

CH.sub.2═CHCH═CH(CH.sub.2).sub.aCHO   (5)

wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1):

R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aCH(OR.sup.2)(OR.sup.3)   (1)

wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.2 and R.sup.3 may form together a divalent hydrocarbon group, R.sup.2-R.sup.3, having 2 to 10 carbon atoms, and “a” is as defined above.

The present invention provides a process for preparing a terminal conjugated alkadienal compound of the following general formula (5):

CH.sub.2═CHCH═CH(CH.sub.2).sub.aCHO   (5)

wherein “a” represents an integer of 1 to 15, from a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1):

R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aCH(OR.sup.2)(OR.sup.3)   (1)

wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, R.sup.2 and R.sup.3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.2 and R.sup.3 may form together a divalent hydrocarbon group, R.sup.2-R.sup.3, having 2 to 10 carbon atoms, and “a” is as defined above.

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention relates to a process for preparing a (2-cyclopentenyl)acetate ester compound of general formula (2) as described herein, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of general formula (1) as described herein to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound of general formula (2). The present invention also relates to a process for preparing a (2-cyclopentenyl)acetic acid compound of general formula (3) as described herein, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound of general formula (2) to form the (2-cyclopentenyl)acetic acid compound of general formula (3). The present invention also relates to a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of general formula (1) as described herein.

The present invention relates to a process for preparing a (2-cyclopentenyl)acetate ester compound of general formula (2) as described herein, the process comprising: subjecting a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of general formula (1) as described herein to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to form the (2-cyclopentenyl)acetate ester compound of general formula (2). The present invention also relates to a process for preparing a (2-cyclopentenyl)acetic acid compound of general formula (3) as described herein, the process comprising hydrolyzing the (2-cyclopentenyl)acetate ester compound of general formula (2) to form the (2-cyclopentenyl)acetic acid compound of general formula (3). The present invention also relates to a haloacetaldehyde alkyl 2-cyclopentenyl acetal compound of general formula (1) as described herein.

The present invention provides a production method of α-fluoroacrylate ester, a composition containing a highly-pure fluorocyclopropane derivative and a composition containing highly-pure α-fluoroacrylate ester. The present invention relates to a method of producing a compound represented by the following formula (F), including subjecting a composition containing a compound represented by the following formula (A) to a purification treatment in the order of distillation and washing with an aqueous alkali solution to give a purified product containing a compound represented by the following formula (A), and subjecting the purified product to a thermal decomposition reaction, a composition containing a highly-pure compound represented by the following formula (A), and a composition containing a highly-pure compound represented by the following formula (F), wherein R may be the same or different and is a monovalent hydrocarbon group, and X is a halogen atom: ##STR00001##