3-chlorosalicylic acid

Structural formula
General
Surname	3-chlorosalicylic acid
other names	3-chloro-2-hydroxybenzoic acid
Molecular formula	C 7 H 5 ClO 3
External identifiers / databases
EC number	217-379-5
ECHA InfoCard	100.015.799
PubChem	74585
ChemSpider	67162
Wikidata	Q223071
properties
Molar mass	172.57 g mol −1
Physical state	firmly
Melting point	184-186 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-chlorosalicylic acid is a chemical compound that belongs to both the phenol group and the aromatic carboxylic acid group.

presentation

3-chlorosalicylic acid cannot be obtained directly from salicylic acid because the preferred direction of substitution is the 5-position. Therefore, a sulfonic acid group is introduced first, then the chlorination is carried out and finally desulfonation is carried out.

Production of 3-chlorosalicylic acid with a sulfonic acid as an intermediate.

Furthermore, the synthesis via a Reimer-Tiemann reaction and subsequent oxidation of the aldehyde formed with silver oxide is possible.

Production of 3-chlorosalicylic acid with 3-chlorosalicylaldehyde as an intermediate.

A Kolbe-Schmitt reaction with 2-chlorophenol also gives 3-chlorosalicylic acid, but in a low yield.

Production of 3-chlorosalicylic acid by a Kolbe-Schmitt reaction.

Reactions

Oxidation with potassium persulfate turns 3-chlorosalicylic acid into 3-chlorogentisic acid (melting point 220–223 ° C).

Synthesis of 3-chlorogentisic acid from 3-chlorosalicylic acid.

proof

The reaction with iron (III) chloride gives an intense purple color.

Individual evidence

↑ ^a ^b ^c Data sheet 3-Chlorosalicylic acid from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
↑ NW Hirwe, KN Rana, KD Gavankar: Derivatives of salicylic acid. In: Proceedings of the Indian Academy of Sciences - Section A. 8, 1938, pp. 208-213, doi : 10.1007 / BF03045504 .
↑ ^a ^b R.L.Crawford, SWHutton, PJChapman: "Purification and Properties of gentisates 1,2-dioxygenase from Moraxella osloensis", in: J. Bacteriol. , 1975 , 121 (3), pp. 794-799; PMC 246005 (free full text).
^ ^A ^b N. Walker, GH Wiltshire: The decomposition of 1-chloro- and 1-bromonaphthalene by soil bacteria. In: Journal of General Microbiology. 12 (3), 1955, pp. 478-483, doi : 10.1099 / 00221287-12-3-478 , PMID 14392303 .

[Sigma-1] Data sheet 3-Chlorosalicylic acid from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[Hirwe-2] NW Hirwe, KN Rana, KD Gavankar: Derivatives of salicylic acid. In: Proceedings of the Indian Academy of Sciences - Section A. 8, 1938, pp. 208-213, doi : 10.1007 / BF03045504 .

[Crawford-3] R.L.Crawford, SWHutton, PJChapman: "Purification and Properties of gentisates 1,2-dioxygenase from Moraxella osloensis", in: J. Bacteriol. , 1975 , 121 (3), pp. 794-799; PMC 246005 (free full text).

[Walker-4] A ^b N. Walker, GH Wiltshire: The decomposition of 1-chloro- and 1-bromonaphthalene by soil bacteria. In: Journal of General Microbiology. 12 (3), 1955, pp. 478-483, doi : 10.1099 / 00221287-12-3-478 , PMID 14392303 .