2-Amino-2-methyl-1-propanol → Benzoyl chloride, 3,4,5-trimethoxy-

Participants

Reaction Steps

A solution of 16.2 g (70 mmoles) of 3,4,5-trimethoxybenzoyl chloride (compound 1) in 40 ml of dry methylene chloride was added dropwise to a solution of 12.5 g (140 mmoles) of 2-amino-2-methyl-1-propanol in 50 ml of dry methylene chloride under cooling in an ice-bath for 30 minutes. After completion of the addition, the mixture was stirred for additional 45 minutes and the reaction solution was filtered through a glass filter. The filtered cake was washed with methylene chloride and the filtrate was combined with the washing, which was followed by concentration in vacuo. The residue was dissolved in 30 ml of dry toluene, and 6.64 ml (91.0 mmoles) of thionyl chloride was added dropwise thereto under cooling in an ice-bath. The mixture was allowed to warm to room temperature, while being stirred for additional 45 minutes. Subsequently, 20 g of ice and aqueous sodium hydroxide (18 g of NaOH in 60 ml of water) were added to the mixture and then the mixture was extracted with toluene. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. After concentration in vacuo, the residue was crystallized from 70 ml of n-hexane to give 16.8 g (90.6% from compound 1) of the desired compound. Melting point: 87°-89° C.

Provenance & Evidence