2,6-Di-tert-butylphenol → 4-(2-Chloronicotinoyl)2,6-di-tertiary butylphenol

Participants

Reaction Steps

To a solution of 282 g of 2-chloronicotinoyl chloride and 400 g of 2,6-di-tertiary butylphenol in 1000 ml of dichloroethane under ice-cooling is added dropwise a solution of 500 g of anhydrous stannic chloride in 250 ml of dichloroethane with stirring over 50 minutes. The reaction temperature is kept below 5° C. during the addition. After completion of the addition, the mixture is stirred at room temperature for 1.5 hours. The resulting reaction mixture is poured into ice-cold water and stirred for a while. The organic layer is separated, washed with water, dried and then concentrated. The obtained residue is recrystallized from an aqueous solution of 80% methanol to give 442 g of 4-(2-chloronicotinoyl)-2,6-di-tertiary butylphenol as pale yellow crystals, melting at 135°-137° C.

Provenance & Evidence