Aromatic thioether acylation method

Details Aromatic thioether acylation method Aromatic thioether acylation method

1998-08-03

2000-09-19

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

568 41, 568 38, 568 56, C07C31914

Patent

active

061214965

DESCRIPTION:

BRIEF SUMMARY
In its preferred variant, the invention resides in a process for the condensation of acetic anhydride or acetyl chloride with thioanisole.
In the following account of the present invention, the term "aromatic thioether" means an aromatic compound of which a hydrogen atom directly linked to the aromatic nucleus is replaced by a thioether group, and the term "aromatic compound" means the conventional notion of aromaticity as defined in the literature, particularly by Jerry MARCH, Advanced Organic Chemistry, 4th edition, John Wiley and Sons, 1992, pp 40 et seq.
A process has been found, and this constitutes the subject matter of the present invention, for the acylation of an aromatic thioether, characterised in that it consists in reacting said thioether with an acylating agent chosen from the group formed by the halides of carboxylic acids and the anhydrides of carboxylic acids, in the presence of an effective quantity of an acid zeolite.
More specifically, the present invention relates to a process for the acylation of an aromatic thioether having the general formula (I): ##STR1## in which: A symbolises the radical of a ring forming all or part of an aromatic, monocyclic or polycyclic carbocyclic system, a system containing at least one SR' group: said cyclic radical may bear one or more substituents, carbon atoms, which may be a saturated or unsaturated, linear or branched acyclic aliphatic radical, a saturated, unsaturated or aromatic, monocyclic or polycyclic cycloaliphatic radical, a saturated or unsaturated, linear or branched aliphatic radical bearing a cyclic substituent,
In the present disclosure, the term "thioether groups" designates, in a simplified manner, groups of the --S--R' type in which R' has the meaning given above. R' therefore represents both an acyclic or cycloaliphatic, saturated, unsaturated or aromatic aliphatic radical and a saturated or unsaturated aliphatic radical bearing a cyclic substituent.
The aromatic thioether used in the process of the invention corresponds to formula (I) in which R' represents a saturated or unsaturated, linear or branched acyclic aliphatic radical.
More preferably, R' represents a linear or branched alkyl radical having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms: the hydrocarbon chain may optionally be interrupted by a heteroatom (for example, oxygen), by a functional group (for example --CO--) and/or may bear a substituent (for example, a halogen).
The saturated or unsaturated, linear or branched acyclic aliphatic radical may optionally bear a cyclic substituent. The term ring preferably means a saturated, unsaturated or aromatic carbocyclic ring, preferably cycloaliphatic or aromatic, particularly cycloaliphatic containing 6 carbon atoms in the ring or benzene ring.
The acyclic aliphatic radical may be linked to the ring by a valency bond, a heteroatom or a functional group, and examples are given below.
The ring may optionally be substituted and examples of cyclic substituents may include, inter alia, substituents such as R.sub.1 the meaning of which is specified for formula (Ia).
R' may also represent a carbocyclic radical which is saturated or contains 1 or 2 unsaturations in the ring, generally having 3 to 8 carbon atoms, preferably 6 carbon atoms in the ring, said ring may be substituted with substituents such as R.
R' may also represent an aromatic carbocyclic radical, preferably monocyclic, generally having at least 4 carbon atoms, preferably 6 carbon atoms in the ring; said ring may be substituted with substituents such as R.
The process of the invention applies more particularly to aromatic thioethers of formula (I) in which R' represents a linear or branched alkyl radical having 1 to 4 carbon atoms or a phenyl radical.
Examples of radicals R' preferred according to the invention include methyl and ethyl radicals.
In the general formula (I) of aromatic thioethers, the radical A may represent the radical of an aromatic, monocyclic, carbocyclic compound having at least 4 carbon atoms and preferably 6 carbon atoms, or the radical of a

REFERENCES:
patent: 4593125 (1986-06-01), Davenport
patent: 4638070 (1987-01-01), Lambelin
J Chem Soc Chem Commun by Kawada "Firedel-Crafts Acylation" (14), pp. 1157-1158, 1993.
Stud. Surf. Sci. Catal. (Heterog. Catal. Fine Chem.) vol. 41, 1988, pp. 241-248, XP002004930, B. Coq et al., see pp. 241, 242, 245-248.

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