Process for preparing acylaromatic compounds
AssigneeCatalytica Pharmaceuticals, Inc.
InventorsJohn Myron Gruber, Robert Seemayer
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Abstract
This invention provides a process for preparing acylaromatics comprising reacting an aromatic compound with a carboxylic acid in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid. In one embodiment, the invention provides a process for preparing a para-acyl phenoxyethylamine comprising the steps of reacting a 2-phenoxyethyl compound bearing a leaving group on the ethyl 1-position with a carboxylic acid in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid, to form apara-acyl phenoxyethyl intermediate bearing the leaving group; and reacting the para-acyl phenoxyethyl intermediate with an amine that substitutes for the leaving group to form the para-acyl phenoxyethylamine.
Claims33
A process for the preparation of an acylaromatic compound of the formula R.sup.1 C(.dbd.O)Ar.sup.1 comprising reacting an aromatic compound of the formula HAr.sup.1, wherein Ar.sup.1 is an aryl group, with a carboxylic acid of the formula R.sup.1 C(.dbd.O)OH, wherein R.sup.1 is a hydrocarbyl group, in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid, to form the acylaromatic compound.
A process for the preparation of apara-acylphenyl ether compound of the formula ##STR25## comprising reacting a phenyl ether compound of the formula ##STR26## wherein R.sup.5 is a hydrocarbyl group,
- Z is a substituent selected from halo, hydrocarbyl, alkoxy, and aryloxy substituents, and
- n is an integer from 0 to 4, wherein when n is greater than 1, the Z substituents may be the same or different,
- with a carboxylic acid of the formula ##STR27## wherein R.sup.1 is a hydrocarbyl group, in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid, to form the para-acylphenyl ether compound.
A process for the preparation of apara-acyl phenoxyethylamine of the formula ##STR28## comprising:
- reacting a 2-phenoxyethyl compound of the formula ##STR29## wherein X is a leaving group capable of substitution by an amine of the formula HNR.sup.3 R.sup.4, with a carboxylic acid of the formula ##STR30## wherein R.sup.1 is a hydrocarbyl group, in the presence of a reaction medium comprising polyphosphoric acid and a strong protic acid, to form a para-acyl phenoxyethyl intermediate of the formula ##STR31## and reacting the para-acyl phenoxyethyl intermediate with an amine of the formula HNR.sup.3 R.sup.4 wherein
- R.sup.3 and R.sup.4 are independently selected from hydrogen and hydrocarbyl groups, or
- R.sup.3 and R.sup.4 taken together form a divalent hydrocarbyl group, to form the para-acyl phenoxyethylamine.
Dependencies are inferred from the claim text.