Process for preparing substituted aromatic carboxylic acids
AssigneePerkinElmer Health Sciences, Inc.
InventorsCrist N. Filer, Terence P. Kelly, Chrisopher Wright
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Abstract
A process for preparing an aromatic carboxylic acid having a heteroatom containing substituent is provided that includes reaction in a vessel of an aromatic precursor having an aromatic core with at least one heteroatom containing substituent and at least one hydrogen extending from the core, with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety. The aromatic acetonitrile is exposed to an oxidizing agent under conditions to convert the acetonitrile moiety to a carboxylic acid group to prepare the aromatic carboxylic acid having the heteroatom containing substituent.
Claims15
A process of preparing an aromatic carboxylic acid having a heteroatom containing substituent ortho, meta, or β of said carboxylic acid comprising:
- reacting in a reaction vessel an aromatic precursor having an aromatic core having at least one heteroatom containing substituent and at least one hydrogen with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety and at least one heteroatom containing substituent, said heteroatom containing substituent ortho, meta, or β of said acetonitrile moiety;
- exposing said aromatic acetonitrile having at least one heteroatom containing substituent to an oxidizing agent under conditions to convert the acetonitrile moiety into a carboxylic acid group to prepare said aromatic carboxylic acid having at least one heteroatom containing substituent ortho, meta, or β of said carboxylic acid.
A process of preparing an aromatic carboxylic acid having a heteroatom containing substituent comprising:
- performing a two step reaction
- wherein a first step comprises reacting (Z)n—Ar—H with XCH2CN to produce (Z)n—Ar—CH2CN;
- and
- wherein a second step comprises reacting said (Z)n—Ar—CH2CN under oxidizing conditions;
- where Ar is an aromatic or polyaromatic core;
- Z is independently in each instance a heteroatom containing substituent of —NO2, —SO3-M+, —SO3R, or —OR;
- n is an integer value of between 1 and 4;
- X is Cl, Br or I;
- M+ is H+ or alkali metal cations;
- R is C1-C6 alkyl group, to form an aromatic carboxylic acid having a heteroatom containing substituent ortho, meta, or β of said acid.
Dependencies are inferred from the claim text.