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).

This disclosure relates to methods of synthesizing certain lipoxin analogs (e.g., lipoxin mimetics, etc.) and pharmaceutical compositions comprising these pro-resolving compounds. Methods of administering the lipoxin mimetics (e.g., lipoxin A4 mimetics, lipoxin B4 mimetics, etc.) to patients in need thereof are also provided.

This disclosure relates to methods of synthesizing certain lipoxin analogs (e.g., lipoxin mimetics, etc.) and pharmaceutical compositions comprising these pro-resolving compounds. Methods of administering the lipoxin mimetics (e.g., lipoxin A4 mimetics, lipoxin B4 mimetics, etc.) to patients in need thereof are also provided.

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 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).

An aim of the present disclosure is to provide a method for producing a fluoroalkoxide, said method being more useful than conventional methods, and the like. The aim can be achieved by a method for producing a compound represented by the following formula (1):

##STR00001## (wherein R.sup.1 is a fluoroalkyl group optionally containing an oxygen atom between carbon atoms, or a fluoroalkoxy group optionally containing an oxygen atom between carbon atoms, and each R.sup.2 is identical to or different from each other and is a hydrocarbon group), the method comprising the step of reacting a compound represented by the following formula (2):

##STR00002## with a compound represented by the following formula (3):

.sup.⊖F.sup.⊕NR.sup.2).sub.4  (3).

An aim of the present disclosure is to provide a method for producing a fluoroalkoxide, said method being more useful than conventional methods, and the like. The aim can be achieved by a method for producing a compound represented by the following formula (1):

##STR00001## (wherein R.sup.1 is a fluoroalkyl group optionally containing an oxygen atom between carbon atoms, or a fluoroalkoxy group optionally containing an oxygen atom between carbon atoms, and each R.sup.2 is identical to or different from each other and is a hydrocarbon group), the method comprising the step of reacting a compound represented by the following formula (2):

##STR00002## with a compound represented by the following formula (3):

.sup.⊖F.sup.⊕NR.sup.2).sub.4  (3).

A method for producing a methanol precursor, methyl trifluoroacetate, having high-purity includes the steps of (a) preparing methyl bisulfate by mixing a catalyst with an acid solution comprising a sulfur-containing acid to provide a first mixture and supplying methane gas to the first mixture to prepare the methyl bisulfate; and (b) preparing methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3) by adding trifluoroacetic acid (CF.sub.3CO.sub.2H) to the first mixture including the methyl bisulfate to provide a second mixture and distilling the second mixture under heating to prepare, separate and purify the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3). Methanol may be produced by adding water to the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3). A methyl ester represented by Formula 2 below may be produced by adding a carboxylic acid represented by Formula 1 below to the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3):
R.sub.1CO.sub.2H  (1), where R.sub.1 is selected from C.sub.1-C.sub.10 alkyl groups,
R.sub.1CO.sub.2CH.sub.3  (2), where R.sub.1 is as defined in Formula 1.

A method for producing a methanol precursor, methyl trifluoroacetate, having high-purity includes the steps of (a) preparing methyl bisulfate by mixing a catalyst with an acid solution comprising a sulfur-containing acid to provide a first mixture and supplying methane gas to the first mixture to prepare the methyl bisulfate; and (b) preparing methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3) by adding trifluoroacetic acid (CF.sub.3CO.sub.2H) to the first mixture including the methyl bisulfate to provide a second mixture and distilling the second mixture under heating to prepare, separate and purify the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3). Methanol may be produced by adding water to the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3). A methyl ester represented by Formula 2 below may be produced by adding a carboxylic acid represented by Formula 1 below to the methyl trifluoroacetate (CF.sub.3CO.sub.2CH.sub.3):
R.sub.1CO.sub.2H  (1), where R.sub.1 is selected from C.sub.1-C.sub.10 alkyl groups,
R.sub.1CO.sub.2CH.sub.3  (2), where R.sub.1 is as defined in Formula 1.

Provided is a method of producing various 2-((meth)allyloxymethyl)acrylic acid derivatives in high yields with no need to load a raw material in a large excess for improving a reaction conversion ratio, and without use of a catalyst having high toxicity or a strong acid catalyst. Also provided are powder compounds that may be utilized as raw materials for synthesizing various chemical products. A method of producing a 2-((meth)allyloxymethyl)acrylic acid derivative includes causing the powder of a salt of a 2-((meth)allyloxymethyl)acrylic acid anion and an alkali metal cation (component A), and a halide (component B) to react with each other to produce a 2-((meth)allyloxymethyl)acrylic acid derivative. The 2-((meth)allyloxymethyl)acrylic acid alkali metal salt powder is the powder of a salt of a 2-((meth)allyloxymethyl)acrylic acid anion and an alkali metal cation, and has a bulk density of 0.50 g/mL or more, or a water content of 0.05 wt % or less.