83. α-Acetylbutyrolactone

Nomenclature

CAS number: 517-23-7
3-Acetyldihydro-2(3H)-furanone; α-(2-hydroxyethyl)acetoacetic acid γ-lactone; α-acetyl-γ-hydroxybutyric acid γ-lactone; α-acetobutyrolactone.
C6H8O3; mol wt 128.13.
C 56.24%, H 6.29%, O 37.46%.

Description and references

Prepn from sodium acetoacetate and ethylene oxide in abs alcohol: Knunyantz et al., C. R. Acad. Sci. USSR [N.S.] 1, 312 (1934), C.A. 28, 4383 (1934); Feofilaktov, Onishchenko, J. Gen. Chem. USSR 9, 304 (1939), C.A. 34, 378 (1940); Forman; Johnson, US 2397134 and US 2443827 (1946, 1948 both to U.S. Industrial Chemicals).

Chemical structure

Properties

Liquid; ester-like odor. Soly in water: 20% v/v; soly of water in lactone: 12% v/v. d420 1.1846; d2020 1.185-1.189; bp30 142-143°; bp18 130-132°; bp5 107-108°. nD20 1.4562 (Knunyantz); nD20 1.4590 (Feofilaktov). Acquires a blue to bluish-purple color when in contact with iron.

Caution

Irritating to skin, mucous membranes.

Use

In synthesis of 3,4-disubstituted pyridines; of 5-(β-hydroxethyl)-4-methylthiazole.