2-(4-chloro-2,6-dimethyl-phenyl)propanedinitrile.

2-(4-chloro-2,6-dimethyl-phenyl)propanedinitrile.

This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R.sup.6SO.sub.2R.sup.7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R.sup.5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

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The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R.sup.6SO.sub.2R.sup.7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R.sup.5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

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Provided is a method for producing a methyl-adduct compound, the method including methylating, in the presence of potassium carbonate and dimethyl carbonate, a dinitrile compound represented by Formula (1) below to obtain a methyl-adduct compound represented by Formula (2) below:

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where in Formula (2), R.sup.1R.sup.4 each independently represent hydrogen or methyl, and from one to three of R.sup.1R.sup.4 are each methyl.

Provided is a method for producing a methyl-adduct compound, the method including methylating, in the presence of potassium carbonate and dimethyl carbonate, a dinitrile compound represented by Formula (1) below to obtain a methyl-adduct compound represented by Formula (2) below:

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where in Formula (2), R.sup.1R.sup.4 each independently represent hydrogen or methyl, and from one to three of R.sup.1R.sup.4 are each methyl.

The present invention relates to an organic material and to an electronic device comprising the organic material, particularly to an electroluminescent device, particularly to an organic light emitting diode (OLED), wherein the semiconducting material comprises a multiple-substituted phenyl moiety, an aryl moiety with at least two fused rings, a polar moiety and optional linkers between these moieties.

The present invention relates to an organic material and to an electronic device comprising the organic material, particularly to an electroluminescent device, particularly to an organic light emitting diode (OLED), wherein the semiconducting material comprises a multiple-substituted phenyl moiety, an aryl moiety with at least two fused rings, a polar moiety and optional linkers between these moieties.