3-Hydroxy-2-naphthoic acid → 3-Hydroxynaphthalene-2-carbonyl chloride

Participants

Reaction Steps

To 30 grams (0.16 moles) of 2-hydroxy-3-naphthoic acid in 125 milliliters of methylene chloride was added 24 grams of thionyl chloride. The reaction mixture was maintained at reflux under a nitrogen atmosphere. After 4 hours, a dark brown solution of 2-hydroxy-3-naphthoic acid chloride was obtained. The solution was cooled to room temperature, placed in a 125 milliliter pressure equalizing funnel, and added slowly to a 200 milliliter methylene chloride solution of 24 grams of N,N-diethylaniline and 27 grams of 2,3-dichloroaniline (0.16 moles). The mixture was heated to reflux. The reaction was substantially complete after approximately 3 hours; and allowing the reaction to continue for up to 20 hours was not observed to affect the product. Half of the reacting solvent was distilled off and 50 to 100 milliliters of ethanol was introduced. After cooling the mixture to room temperature, the precipitated product was collected by filtration and washed twice with 50 milliliter portions of methanol. The crude product was then recrystallized from a mixture of duimethylformamide and methanol. Yield of the coupler compound 2-hydroxy-3-naphtho-2',3'-dichloroanilide was 37 grams (70 percent). The coupler compound exhibited the following properties:

Provenance & Evidence