4-Methylsalicylic acid

4-Methylsalicylic acid
Names
	Preferred IUPAC name 2-Hydroxy-4-methylbenzoic acid
	Other names m-Cresotic acid; 2,4-Cresotic acid; m-Cresotinic acid; 2-Hydroxy-p-toluic acid
Identifiers
CAS Number	50-85-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:20450;
ChemSpider	5584;
ECHA InfoCard	100.000.063
EC Number	200-068-3;
KEGG	C14103;
PubChem CID	5788;
UNII	4H0106V3D3 ;
CompTox Dashboard (EPA)	DTXSID30198166 ;
	InChI InChI=1S/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11) Key: NJESAXZANHETJV-UHFFFAOYSA-N; InChI=1/C8H8O3/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4,9H,1H3,(H,10,11) Key: NJESAXZANHETJV-UHFFFAOYAQ;
	SMILES CC1=CC(=C(C=C1)C(=O)O)O;
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	white solid
Melting point	177 °C (351 °F; 450 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Methylsalicylic acid is an organic compound with the formula CH₃C₆H₃(CO₂H)(OH). It is a white solid that is soluble in basic water and in polar organic solvents. Its functional groups include a carboxylic acid and a phenol group. It is one of four isomers of methylsalicylic acid, including the naturally occurring 6-methylsalicylic acid. The compound has few applications. It is produced by carboxylation of sodium para-cresolate:^[1] CH₃C₆H₄ONa + CO₂ → CH₃C₆H₃(CO₂Na)OH

It has been prepared by hydroxylation of 4-methylbenzoic acid.^[2]

References

^ Ritzer, Edwin; Sundermann, Rudolf (2000). "Hydroxycarboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_519. ISBN 3527306730.
^ Zhang, Yang-Hui; Yu, Jin-Quan (2009). "Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O₂ or air". Journal of the American Chemical Society. 131 (41): 14654–14655. doi:10.1021/ja907198n. PMID 19788192.

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[1] Ritzer, Edwin; Sundermann, Rudolf (2000). "Hydroxycarboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_519. ISBN 3527306730.

[2] Zhang, Yang-Hui; Yu, Jin-Quan (2009). "Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O₂ or air". Journal of the American Chemical Society. 131 (41): 14654–14655. doi:10.1021/ja907198n. PMID 19788192.

[1]

[2]

See also

References