Sodium Hydroxide → N-(3,5-Di-tert-butyl-4-hydroxyphenyl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 11.05 grams (0.05 mole) of 4-amino-2,6-di-tert-butylphenol in 60 ml of chloroform was added with stirring 5.75 grams (0.05 mole) of methanesulfonyl chloride over a 5-minute period. The reaction mixture was heated to 35° C for 15 minutes followed by the dropwise addition of 8.0 grams (0.05 mole) of a 25% aqueous sodium hydroxide solution and finally heating at 47° C for 30 minutes. After cooling to room temperature, the chloroform layer was separated, washed with water and dried over 4A Molecular Sieves and filtered. The solvent was removed in vacuo, and the residue was washed with hexane leaving 5.8 grams of a crude pink product. Recrystallization from toluene and again from ethylene dichloride gave 2.7 grams of colorless crystals melting at 149°-151° C. (Compound 2)

Provenance & Evidence