Aldrich-Boranes, Inc.

Clinton Fisher Lane

Hal Leslie Myatt

Organic compounds containing a carboxylic acid or carboxylic acid anhydride group are reduced when contacted with an alkali metal borohydride and a boron trihalide in a liquid medium in which diborane is soluble in the form of a labile borane adduct. Hydrolysis of the reaction mixture then provides a useful synthesis of the corresponding carbinols. The alkali metal borohydride-boron trihalide reagent may either be preformed and reacted subsequently with an organic compound containing a carboxylic acid or anhydride group, or the alkali metal borohydride-boron trihalide reagent may be produced in the presence of an organic compound containing a carboxylic acid or anhydride group. This development makes it possible to synthesize a wide variety of carbinols which are valuable and useful intermediates in organic synthesis.

Process for the preparation of carbinols

Organic compounds containing both an amino group and a carboxylic acid group are reduced when treated with boron trifluoride followed by diborane, a borane-ether or borane-organic sulfide complex. The presence of the boron trifluoride is responsible for an increase in the rate of reduction of the carboxylic acid group and eliminates the need for the large excess of the borane complex normally required due to the competing formation of boron-nitrogen compounds. Hydrolysis of the reaction mixture provides a useful and convenient method for separating the corresponding amino alcohol.

Growing community of inventors

Franklin, WI, United States of America

Clinton Fisher Lane