Benzene → HCID 21499160, compound

Participants

Reaction Conditions

Reaction Steps

An amount of 163.0 g of 3,5-dichlorophenol is dissolved in 200 ml of benzene and 79.1 g of anhydrous pyridine; there is then added dropwise at 5°-15° C with stirring, in the course of 1 hour, a solution of 134.6 g of caproic acid chloride in 200 ml of benzene. The temperature of the reaction mixture is allowed to rise to 20° C; the precipitated pyridine hydrochloride is filtered off, the benzene solution washed with water and, after drying over sodium sulphate, completely concentrated in a water-jet vacuum. The caproic acid-3,5-dichlorophenyl ester remaining (255 g) is heated to 60° C, and an addition then made to it at this temperature in the course of 10 minutes, with stirring, of 400 g of anhydrous aluminium chloride. After 5 hours, the liquid reaction mixture is poured, as stirring is maintained, into 3 liters of ice water. The initially oily precipitate fully crystallises during subsequent stirring. It is filtered off, washed with water and dried in vacuo to obtain 210.7 g of 2-hydroxy-4,6-dichlorocaprophenone, M.P. 39°-41° C.

Provenance & Evidence