Methods for producing cyclopropane carboxylates

Details Methods for producing cyclopropane carboxylates Methods for producing cyclopropane carboxylates

2000-06-16

2002-08-27

Killos, Paul J. (Department: 1625)

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

Organic compounds

Carboxylic acid esters

C560S234000

Reexamination Certificate

active

06441220

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method for producing a cyclopropanecarboxylate.
2. Description of Related Art
As for a method for producing a cyclopropanecarboxylic acid ester by transesterification reaction, for example, a method employing a sodium alkoxide catalyst has been disclosed (JP-A-52-128336) as well as a large number of the studies on the alkoxide catalysts of transition metals such as Ti (JP-A-52-128337, German Patent No. 2822472, British Patent No. 2005269).
However, in any of these transesterification reaction all catalysts required anhydrous conditions due to its stability in the presence of moisture, and hence should be stored, handled and reacted in an anhydrous condition, and thus they are not always satisfactory for an industrial manufacturing.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a method for producing a cyclopropanecarboxylate readily in good yield by conducting a transesterification reaction between a cyclopropanecarboxylate and a monohydroxy compound in the presence of an alkali metal hydroxide, which method is advantageous in that said alkali metal hydroxide is not only inexpensive and readily available but also stable and can be readily handled.
Thus the present invention provides
a method for producing a cyclopropanecarboxylate of formula (
3
):
wherein R
1
, R
2
, R
3
, R
4
and R
5
each independently represent:
a hydrogen atom, halogen atom,
an optionally substituted alkyl group,
an optionally substituted alkenyl group,
an optionally substituted aralkyl group or
an optionally substituted aryl group; and
R
7
represents:
an optionally substituted alkyl group,
an optionally substituted aralkyl group, or
an optionally substituted aryl group,
which comprises:
contacting a cyclopropanecarboxylate of the formula (
1
)
wherein R
1
, R
2
, R
3
, R
4
and R
5
are as defined above, and
R
6
represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group,
with a monohydroxy compound of the formula (
2
):
R
7
OH
  (2)
wherein R
7
is the same as defined above, in the presence of an alkali metal


REFERENCES:
patent: 3647857 (1972-03-01), Morgan
patent: 3873716 (1975-03-01), Fanta
patent: 3882242 (1975-05-01), Crawford
patent: 3976663 (1976-08-01), Fanta
patent: 4053629 (1977-10-01), Fanta
patent: 4116998 (1978-09-01), Makinson et al.
patent: 4283414 (1981-08-01), Harney et al.
patent: T102908 (1983-04-01), Halpern et al.
patent: 4418202 (1983-11-01), Fayter, Jr. et al.
patent: 4976892 (1990-12-01), Jeromin et al.
patent: 2744641 (1979-04-01), None
patent: 0992479 (2000-04-01), None
patent: 2584611 (1987-01-01), None
patent: 2005269 (1979-04-01), None
patent: 52128336 (1977-10-01), None
patent: 52128337 (1977-10-01), None
patent: 53130627 (1978-11-01), None
patent: 53147040 (1978-12-01), None
patent: 5459265 (1979-05-01), None
patent: 5481235 (1979-06-01), None
patent: 7330671 (1995-12-01), None
patent: 9239270 (1997-09-01), None
Chinese Journal of Chemistry, vol. 15, No. 1, 1997, pp. 90-93.
J. Org. Chem., vol. 61, 1996, pp. 3088-3090.
Bull. Chem. Soc. Jpn., vol. 66, No. 6, 1993, pp. 1863-1864.
Chem. Lett., vol. 3, No. 44, 1995, p. 246.
The 22nd Symposium on Rare Metal, 1993, p. 44.
M. Smith, “The Cyclopropane Group”, Rodd's Chemistry of Carbon Compounds, Second Ed. (1967) Vol. II, Part A, Chapter 2, pp. 19-71.*
Aldrich Catalog Handbook of Fine Chemicals 1996-1997 (Aldrich Chemical Company).*
Michael P. Doyle et al, “Rearrangements of Oxocyclopropanecarboxylate Esters to Vinyl Ethers. Disparate Behavior of Transition-Metal Catalysts”, J. Org. Chem., vol. 47 (1982), pp. 5326-5339.

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