1-Naphthol → 1-(1-Naphthyloxy)-3-(tert-butylamino)-2-propanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 7.9 parts of α-naphthol 0.2 part of potassium hydroxide was added, and the mixture was heated at 160° C. for 24 hours. The reaction mixture was cooled and then dissolved in 100 parts of ether. The solution was washed twice with 50 parts of 2N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and made alkaline by addition of 2N-sodium hydroxide aqueous solution. Extraction was conducted three times with 50 parts of benzene, and the extract was dried over anhydrous sodium sulfate. Then benzene was distilled off and the residue was solidified by drying under reduced pressure. The solid residue was subjected to distillation under reduced pressure. As a result 5 parts of 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol boiling at 175°-180° C. under 1.5 mm Hg were obtained. A part of the product was dissolved in 5 parts of anhydrous ether and the product was converted to a hydrochloride by adding a hydrochloric acid gas to the resulting ether solution. The hydrochloric was recrystallized twice from a mixed solvent of ethyl acetate and ether. As a result 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol hydrochloride having a melting point of 182°-184° C was obtained.

Provenance & Evidence