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##

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##

A fluorine-containing ether compound represented by R.sup.1R.sup.2CH.sub.2R.sup.3CH.sub.2R.sup.4R.sup.5 is provided. (R.sup.3 is a perfluoropolyether chain; R.sup.1 and R.sup.5 are each independently any one of an alkyl group that may have a substituent, an organic group having at least one double bond or at least one triple bond, and a hydrogen atom; and R.sup.2CH.sub.2R.sup.3 is represented by Formula (2), and R.sup.3CH.sub.2R.sup.4 is represented by Formula (3))

-[A]-[B]OCH.sub.2R.sup.3 (2)

R.sup.3CH.sub.2O[C]-[D]- (3)

([A] is represented by Formula (4), [B] is represented by Formula (5), [C] is represented by Formula (6), [D] is represented by Formula (7), and in the formula, a and b are integers of 0 to 2, c is an integer of 2 to 5, d and f are integers of 0 to 2, and e is an integer of 2 to 5, and at least one of b and d in the formula is 1 or more)

##STR00001##

A fluorine-containing ether compound represented by R.sup.1R.sup.2CH.sub.2R.sup.3CH.sub.2R.sup.4R.sup.5 is provided. (R.sup.3 is a perfluoropolyether chain; R.sup.1 and R.sup.5 are each independently any one of an alkyl group that may have a substituent, an organic group having at least one double bond or at least one triple bond, and a hydrogen atom; and R.sup.2CH.sub.2R.sup.3 is represented by Formula (2), and R.sup.3CH.sub.2R.sup.4 is represented by Formula (3))

-[A]-[B]OCH.sub.2R.sup.3 (2)

R.sup.3CH.sub.2O[C]-[D]- (3)

([A] is represented by Formula (4), [B] is represented by Formula (5), [C] is represented by Formula (6), [D] is represented by Formula (7), and in the formula, a and b are integers of 0 to 2, c is an integer of 2 to 5, d and f are integers of 0 to 2, and e is an integer of 2 to 5, and at least one of b and d in the formula is 1 or more)

##STR00001##

A process for preparing 4-penten-2-ynal of the following formula (2):

CH.sub.2CHCCCHO(2)

the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1):

CH.sub.2CHCCCH(OR.sup.1)(OR.sup.2)(1)

wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms,
to obtain 4-penten-2-ynal (2).

##STR00001##

A process for preparing 4-penten-2-ynal of the following formula (2):

CH.sub.2CHCCCHO(2)

the process comprising a step of hydrolyzing a 5,5-dialkoxy-1-penten-3-yne compound of the following general formula (1):

CH.sub.2CHCCCH(OR.sup.1)(OR.sup.2)(1)

wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms,
to obtain 4-penten-2-ynal (2).

##STR00001##

A process for preparing a dienynal compound of the following general formula (2): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCHO (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.sub.2CHCCCHCH(CH.sub.2).sub.nCH(OR.sup.1)(OR.sup.2) (1) wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, mere preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

##STR00001##

A process for preparing a dienynal compound of the following general formula (2): CH.sub.2CHCCCHCH(CH.sub.2).sub.nCHO (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.sub.2CHCCCHCH(CH.sub.2).sub.nCH(OR.sup.1)(OR.sup.2) (1) wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, mere preferably 1 to 4, or R.sup.1 and R.sup.2 may be bonded to each other to form a divalent hydrocarbon group, R.sup.1-R.sup.2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).

##STR00001##

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).

The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2X.sup.1 (1) and (ii) an alkyne compound of the following formula (2): X.sup.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (2) to a coupling reaction to form a silane compound of the following formula (3): YZCR.sup.1CR.sup.2(CH.sub.2).sub.2CCSi(R.sup.3)(R.sup.4)(R.sup.5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).