2,3-Dimethylphenol → Xibenolol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6.5 parts of 1-(tert.butyl)-3-azetidinol and 6.7 parts of 2,3-xylenol 0.2 part of sodium 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 2 N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2 N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and was made alkaline by addition of 2 N-sodium hydroxide aqueous solution. The solution was cooled and agitated to form crystals. The resulting crystals were dried and recrystallized twice from ether to yield 9.2 parts of 1-(2',3'-dimethylphenyloxy)-3-(tert.-butylamino)-2-propanol having a melting point of 57° C.

Provenance & Evidence