Abstract

(1a; R = Et) [638-07-3] C6H9ClO3 (MW 164.60) (1b; R = Me) [32807-28-6] C5H7ClO3 (MW 150.57) (1c; R = i-Pr) [41051-20-1] C7H11ClO3 (MW 178.63) (1d; R = t-Bu) [74530-56-6] C8H13ClO3 (MW 192.66) (highly functionalized four-carbon building block for organic synthesis1) Physical Data: (1a) mp −8.5 °C; bp 95 °C/10 mmHg; fp 92 °C; d 1.212 g cm−3. (1b) mp 14 °C; bp 50 °C/1 mmHg; fp 107 °C; d 1.287 g cm−3. (1c) mp 10 °C; bp 64 °C/1.65 mmHg; fp 86 °C; d 1.152 g cm−3. (1d) bp 101 °C/15 mmHg; fp 41 °C; d 1.130 g cm−3. Form Supplied in: the alkyl 4-chloroacetoacetates are colorless liquids. Solubility: sol most organic solvents. The ethyl ester (1a) is 12% enolized in the pure liquid, and highly enolized (60% in CCl4) in nonpolar solvents.2 Preparative Methods: the industrial production of the esters is made exclusively by chlorination of diketene followed by reaction of the intermediate acid chloride with the corresponding alcohol.3 Handling, Storage, and Precautions: these reagents are lachrymators of moderate toxicity; use in a fume hood.

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