Acetic Acid → 3-(2-Hydroxy-4-methylbenzoyl)benzoic acid

Reaktionsgleichung

C(O[C:8]1[CH:24]=[CH:23][C:11]([C:12]([C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=[O:18])=[O:13])=[C:10](C)[CH:9]=1)CCCCC.[C:26](O)(=O)C.S(=O)(=O)(O)O.[OH2:35]>>[OH:35][C:10]1[CH:9]=[C:8]([CH3:26])[CH:24]=[CH:23][C:11]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=[O:18])=[O:13]

Komponenten

Edukt 4

HCID 176Acetic Acid

HCID 962Water

HCID 1118Sulfuric Acid

HCID 224203873-(4-n-Hexyloxy-2-methylbenzoyl)benzoic acid

Produkt 1

HCID 224203823-(2-Hydroxy-4-methylbenzoyl)benzoic acid

Versuchsvorschrift

A mixture of 3-(2-hydroxy-4-methylbenzoyl)benzonitrile (5.78 g; see Example 29), acetic acid (48 g), and a solution of 75% sulfuric acid (48 g) is refluxed for 3 hours. The resulting mixture is diluted with water (100 ml) and extracted with ether (3×75 ml) followed by methylene chloride (2×75 ml). The combined extracts are dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on silica gel (methylene chloride then hexanes:ether:acetic acid; 50:50:1). The resulting yellow solid is recrystallized from ligroin/isopropyl ether to yield 3-(2-hydroxy-4-methylbenzoyl)benzoic acid (3.62 g), m.p. 198°-215° C.