Process for the preparation of carbinols

Details Process for the preparation of carbinols Process for the preparation of carbinols

1974-09-23

1976-08-31

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260618H, 260611A, 260638A, 260622R, C07C 2900

Patent

active

039781402

ABSTRACT:
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.

REFERENCES:
patent: 2874165 (1959-02-01), Brown
patent: 2945886 (1960-07-01), Brown
patent: 3634277 (1972-01-01), Brown
Brown et al., J.A.C.S., vol. 82, pp. 681-686 (1960).
Brown et al., J.A.C.S., vol. 92, pp. 1637-1644 (1970).
Anhoury et al., J. Chem. Soc., Perkin Trans 1, 191 (1974).

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