Process for the production of 1,2-bis (acyloxylates)

Details Process for the production of 1,2-bis (acyloxylates) Process for the production of 1,2-bis (acyloxylates)

1995-12-29

1997-04-22

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

560112, C07C 6724

Patent

active

056230869

ABSTRACT:
A process for the preparation of 1,2-bis(acyloxyates) comprises acylation of epoxides with carboxylic anhydrides in the presence of a catalytic composition containing a tertiary amine and a carboxylic acid. Preferably, the carboxylic acid is a conjugate acid of the carboxylic anhydride. The carboxylic acid acts as a co-catalyst and its use in conjunction with the tertiary amine significantly increases the rate of reaction and results in higher selectivity. The catalytic composition may be prepared prior to acylation or in situ providing application versatility.

REFERENCES:
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Shvets, V. F., et al., Kinet. Katal., 16(3), pp. 785-788 (1975).
Shvets, V. F., et al., Kinet Katal., 16(2), pp. 425-430 (1975).
Swindell, C. S., et al., J. Org. Chem., 55, p. 3 (1990).
Fraser-Reid, B., et al., J. Amer. Chem. Soc., 107, p. 5576 (1985).
Evans, R. M., et al., J. Chem Soc., p. 248 (1949).
Ali, S., et al., J. Org. Chem., 53, p. 5547, (1988).

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