O-Cresol → HCID 14519867, compound

Participants

Reaction Steps

A mixture of the sodium salts of 2,4-dichlorobenzoic acid (V: X=Cl, R1 =4-Cl) (27.7 g, 130 mmol) and 2-methylphenol (III: R3 =H) (18.9 g, 145 mmol) were dissolved in dry dioxan (300 mL). CuCl (1.3 g, 13 mmol) and tris-[2-(2-methoxyethoxy)ethyl]amine (TDA-1) (4.2 g, 13 mmol) were added, and the mixture was heated at reflux under N2 for 8 hours. Excess solvent was evaporated under reduced pressure, and the residue was diluted with water and filtered. The filtrate was acidified with 2N HCl, and the resulting precipitate was collected, washed well with water and dried to yield 4-chloro-2-(2-methylphenoxy) benzoic acid (IV: R1 =4-Cl, R3 =H) (27 g, 79%), which was suitable for the next step. A sample was crystallized from aqueous MeOH as prisms, mp 158°-159° C. Anal. (C14H11ClO3), C,H,Cl.

Provenance & Evidence