Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.

Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (4), the method including the steps of: hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound (1) to obtain 7-methyl-3-methylene-7-octenal (2); reducing the 7-methyl-3-methylene-7-octenal (2) to obtain 7-methyl-3-methylene-7-octenol (3); and esterifying the 7-methyl-3-methylene-7-octenol (3) to obtain a 7-methyl-3-methylene-7-octenyl carboxylate compound (4). ##STR00001##

The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

Disclosed herein is an efficient, environment friendly and commercially viable process for preparation of chloromethylated compound of formula I in substantially pure form and high yield, from the compound of formula II. The process includes contacting the compound of formula II with a chloromethylating agent generated in-situ by reaction of a formaldehyde precursor and hydrogen chloride, in a suitable solvent/contacting medium and in the presence of a catalytic amount of a short chain/low molecular weight carboxylic acid of formula III. I II III wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the description.

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A process for preparing a dienynal compound of the following general formula (2):
CH.sub.2═CHC≡CCH═CH(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.2═CHC≡CCH═CH(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, 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, and n represents an integer of 0 to 11, to obtain the dienynal compound (2). ##STR00001##

A process for recovering methacrolein and methanol from methacrolein dimethyl acetal. The method comprises a step of contacting a mixture comprising methyl methacrylate and methacrolein dimethyl acetal with a strong acid ion exchange resin in the presence of water. The mixture comprises no more than 0.2 wt % sodium methacrylate.

A method for making cyclopentadiene fuels comprising producing cyclopent-2-en-1-one or a mixture of cyclopent-2-en-1-one from a bio-based source. The cyclopent-2-en-1-one or the mixture of cyclopent-2-en-1-one is hydrogenated, thereby forming cyclopent-2-en-1-ol or a mixture of cyclopent-2-en-1-ol. The cyclopent-2-en-1-ol or the mixture of cyclopent-2-en-1-ol is dehydrated with a dehydrating agent, thereby forming cyclopentadiene or a mixture of cyclopentadiene. The cyclopentadiene or mixture of cyclopentadiene is converted to dicyclopentadiene or dihydrodicyclopentadiene. The dicyclopentadiene or dihydrodicyclopentadiene is hydrogenated, thereby forming tetrahydrodicyclopentadiene. The tetrahydrodicyclopentadiene is isomerized, thereby forming exo-tetrahydrodicyclopentadiene.

A method for making cyclopentadiene fuels comprising producing cyclopent-2-en-1-one or a mixture of cyclopent-2-en-1-one from a bio-based source. The cyclopent-2-en-1-one or the mixture of cyclopent-2-en-1-one is hydrogenated, thereby forming cyclopent-2-en-1-ol or a mixture of cyclopent-2-en-1-ol. The cyclopent-2-en-1-ol or the mixture of cyclopent-2-en-1-ol is dehydrated with a dehydrating agent, thereby forming cyclopentadiene or a mixture of cyclopentadiene. The cyclopentadiene or mixture of cyclopentadiene is converted to dicyclopentadiene or dihydrodicyclopentadiene. The dicyclopentadiene or dihydrodicyclopentadiene is hydrogenated, thereby forming tetrahydrodicyclopentadiene. The tetrahydrodicyclopentadiene is isomerized, thereby forming exo-tetrahydrodicyclopentadiene.

Provided is a one-step method for producing an enol ether using a diketone of a macrocyclic compound as a starting material. A method for producing a compound represented by general formula (I) includes reacting a compound represented by general formula (II) in the presence of a metal catalyst containing at least one metal element selected from the group consisting of magnesium, aluminum, zirconium, titanium, and samarium, and an alcohol containing at least one selected from the group consisting of a primary alcohol and a secondary alcohol to obtain the compound represented by general formula (I). ##STR00001##