Process for the preparation of oxethylmercaptobenzaldehydes and

Details Process for the preparation of oxethylmercaptobenzaldehydes and Process for the preparation of oxethylmercaptobenzaldehydes and

1988-09-20

1990-05-01

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

568 31, 568 41, C07C 51285

Patent

active

049220144

ABSTRACT:
Process for the preparation of oxethylmercaptobenzaldehydes and their oxidation products of the formula (I) ##STR1## in which R denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, m denotes the number 0 or 2, n denotes the number 1 or 2, and p denotes the number 0 or 1, with the proviso that p is 0 if m is 0, and the side-chain --S(0).sub.m --CH.sub.2 --CH.sub.2 --OH is in the ortho and/or para position to the aldehyde or carboxyl group, can be prepared by condensing 1 mole of a halobenzaldehyde of the general formula (II) ##STR2## in which R, X, Y and Z represent hydrogen, fluorine, chlorine, bromine or iodine atoms, with the proviso that R, X, Y and Z can be in total 1, 2 or 3 halogen atoms, where R is a halogen atom if R, X, Y and Z together represent 3 halogen atoms, in aqueous medium with about 1.0 to 1.5 moles of mercaptoethanol (per halogen atom to be exchanged) in the presence of the acid-binding agents at or about 70.degree. C. about 150.degree. C., to give the oxethylmercaptobenzaldehydes and oxidizing these to give the oxethylsulfonylbenzoic acids using at least the amount of hydrogen peroxide necessary in each case at about 40.degree. C. to about 110.degree. C. in the presence of a tungsten(VI) compound as a catalyst.

REFERENCES:
patent: 2763692 (1956-09-01), Gregory
patent: 2802033 (1957-08-01), Gregory
patent: 3098096 (1963-07-01), Feeman
patent: 3787443 (1974-01-01), Erickson
patent: 3956395 (1976-05-01), Meyer
R. Schwyzer et al., Helv. Chim. Acta 67, 1316-1327 (1984).
J. Schwartz, Synth. Commun. 16, 565-570 (1986).

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