Acetic Acid → Ethyl 4-acetoxyacetoacetate

Participants

Reaction Conditions

Reaction Steps

A solution of 1.204 l (21.0 moles) of glacial acetic acid and 2.786 l (20.0 moles) of triethylamine in 8.75 l of methyl isobutyl ketone is heated under reflux, and a solution of 1.498 l (11.2 moles) of ethyl 4-chloro-3-oxobutyrate in 1.75 l of methyl isobutyl ketone is added at the boiling point in the course of 20 minutes. When the addition has ended, the mixture is heated under reflux for a further 30 minutes and cooled to about 5° C. and the salts which have precipitated out are filtered off. The residue on the filter is washed with 4.5 l of methyl isobutyl ketone. The combined filtrates are concentrated in vacuo, and first 2 l of drinking water and then 4 l of a 9% strength sodium bicarbonate solution are added to the residue. The suspension is extracted three times with 4 l of ethyl acetate each time and the combined extracts are dried over 2 kg of sodium sulphate, filtered and concentrated in a rotary evaporator at a bath temperature of 40° C.

Provenance & Evidence