Process for preparing esters of .alpha.-acetyl-.alpha.'-methylsu

Details Process for preparing esters of .alpha.-acetyl-.alpha.'-methylsu Process for preparing esters of .alpha.-acetyl-.alpha.'-methylsu

1978-09-01

1980-03-18

Garner, Vivian

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

Organic compounds

Carboxylic acid esters

560126, 560181, 562479, 562496, 562508, C07C 6730, C07C 6967

Patent

active

041940539

ABSTRACT:
A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.'-(5-methyl-3-oxohexyl)succinate ester, which can then be converted to ibuprofen by procedures now known.

REFERENCES:
patent: 2797237 (1957-06-01), Birbiglia et al.
patent: 3816533 (1974-06-01), Brandstrom
patent: 4096177 (1978-06-01), Baiocchi

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