Ici Americas, Inc.

Ici United States Inc.

Ludwig A Hartmann

John F Stephen

Richard L West

3-Methyl-2-alkylamino-1-halo-1-cyano cyclobutanes are cleaved under acid conditions to form 2-halo-4-formylvaleronitrile and 4-formyl-2-pentenonitrile which can be cyclized to form 2-substituted-5-methylpyridine derivatives. These pyridine derivatives are useful as starting materials in the manufacture of herbicides such as fluazifop-butyl.

Synthesis of 2-substituted-5-methylpyridines from

The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.

Difunctional polyfluoroaromatic derivatives and a process of preparing

Polyfluoroaromatic nitriles

A process for the synthesis of compounds which are known intermediates for the pyridyloxyphenoxy herbicides as well as intermediates used in the process. Propionaldehyde and an acrylic compound, two radily available starting materials, are reacted to form a 2-formylpentanoic compound which is cyclized to a dihydro pyridone which is then oxidized to the 2-hydroxy pyridine. The hydroxypyridine may be halogenated to a 2-halopyridine.

Bispiperidone precursor of 2-substituted-5-methyl-pyridines

A process for the synthesis of compounds which are known intermediates for the pyridyloxyphenoxy herbicies as well as intermediates used in the process. Propionaldehyde and an acrylic compound, two readily available starting materials, are reacted to form a 2-formylpentanoic compound which is cyclized to a dihydro pyridone which is then oxidized to the 2-hydroxy pyridine. The hydroxypyridine may be halogenated to a 2-halopyridine.

Synthesis of 2-substituted-5-methyl-pyridines and intermediates therefor

A process for the synthesis of compounds which are known intermediates for the pyridyloxyphenoxy herbicides as well as intermediates used in the process. Propionaldehyde and an acrylic compound, two readily available starting materials, are reacted to form a 2-formylpentanoic compound which is cyclized to a dihydro pyridone which is then oxidized to the 2-hydroxy pyridine. The hydroxypyridine may be halogenated to a 2-halopyridine.

Synthesis of 2-substituted-5-methyl-pyridines

An improved process for preparing cyano substituted benzyl esters is disclosed. The process involves reacting an acid halide with an aldehyde and a water soluble cyanide in water in the presence of a tetraalkyl ammonium halide wherein each alkyl group contains from 1 to about 4 carbon atoms. The resulting benzyl esters are particularly useful as insecticides.

Preparation of cyano substituted benzyl esters

High molecular weight polyether-sulfones are prepared by reacting a 3,3',5,5'-tetraalkyl-4,4'-dihydroxybiphenyl with 4,4'-dihalodiphenyl sulfone and from about 0 to 30 percent stoichiometric excess of an alkali metal carbonate or bicarbonate compound in the presence of a dipolar aprotic solvent. The polyethersulfone polymers and products made therefrom possess low density and high glass transition temperatures while maintaining good solvent resistance and good tensile, flexural, and hardness properties.

High molecular weight polyethersulfones

Glycidyl ethers prepared from the reaction of 3,3',5,5'-tetraalkyl-4,4'-dihydroxybiphenyl and halohydrin form upon curing resins having high heat distortion temperatures. The ethers have utility in the manufacture of powder coatings, adhesive compositions, laminates and molding compositions.

Glycidyl ethers derived from 3,3',5,5'-tetraalkyl-4,4'-dihydroxybiphenyl

An improved process for the preparation of 3-(4-lithiosulfophenoxy)-1,2-propanediol relatively free from inorganic impurities is represented wherein the subject material is made by reacting lithiosulfophenol with either glycerol monochlorhydrin or epichlorohydrin in aqueous solution in the presence of an alkaline calcium compound and thereafter purifying by removing the calcium sulfate and hydrochloric acid from the aqueous reaction media. The subject material can be obtained at purities of 98% in yields exceeding 70%.

Process for the preparation and purification of

Halogenated dioxolane compounds having perhalogenated groups in the 2-position and other substituted groups, for example, carbamate and nitrate in the 4 and/or 5-position are disclosed. These compounds are useful as tranquilizers.

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Wilmington, DE, United States of America

Ludwig A Hartmann