4-(4-Aminophenyl)cyclohexan-1-one → 4-(4'-Hydroxyphenyl)cyclohexanone

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

200 ml of 4N sulphuric acid were heated to 80° C. in a sulphonation flask and then treated with about 5% of a solution of 37.9 g of 4-(4-aminophenyl)cyclohexanone in 200 ml of 4N sulphuric acid. Subsequently, the remaining solution of 4-(4-aminophenyl)cyclohexanone as well as a solution of 15.2 g of sodium nitrite in 45 ml of water were simultaneously added dropwise to the reaction mixture at 80° C. within 1.5 hours. Thereafter, the mixture was treated dropwise at 80° C. within 30 minutes with a solution of 9 g of sodium nitrite in 27 ml of water and stirred at 80° C. for a further 1 hour. After cooling the reaction mixture to 0° C. the separated crystals were filtered off under suction, washed with 200 ml of cold water and dried up to constant weight at 60° C. in a drying oven under a water-jet vacuum. The crystalline crude product (34.6 g) was suspended in 520 ml of ethyl acetate. The suspension was heated to reflux for 1 hour, treated with 1.7 g of active charcoal and then heated to reflux for a further 1 hour. Subsequently, the mixture was suction filtered (rinsing with 40 ml of warm ethyl acetate) and the filtrate was evaporated in a water-jet vacuum at a bath temperature of 40° C. Drying of the evaporation residue in a water-jet vacuum at 60° C. up to constant weight gave 32.2 g of 4-(4-hydroxyphenyl)cyclohexanone as yellow-brown crystals with m.p. 165°-166° C.

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