Continuous racemization of benzylic alcohols, ethers, and esters

Details Continuous racemization of benzylic alcohols, ethers, and esters Continuous racemization of benzylic alcohols, ethers, and esters

1994-11-21

1995-12-19

Prescott, Arthur C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

564165, 564302, 564304, 564390, C07C 6702, C07C23300, C07C20900

Patent

active

054769647

ABSTRACT:
Benzyl alcohols having a chiral center at the benzylic carbon can be conveniently racemized by treatment with solid acids which are strongly acidic cation exchange materials. Racemization may be effected generally in the range from 20.degree.-150.degree. C. in aqueous or partly aqueous systems in combination with a water-miscible organic solvent to improve solubility of the alcohol. Similar racemizations may be effected for benzyl ethers and esters. This process is valuable for recycling of unwanted enantiomers obtained in the resolution of racemic mixtures.

REFERENCES:
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patent: 5231227 (1993-07-01), Yoneyoshi et al.
Skrebnik, Ramachandran & Brown, J. Org. Chem., 53, 2916, 1988.
Gao & Sharpless, J. Org. Chem., 53, 4081, 1988.
E. J. Corey & G. A. Reichard, Tetrahedron Letters, 30, No. 39, 5207, 1989.
Schneider and Goergens, Tetrahedron: Asymmetry, No. 4, 525, 1992.

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