9161. Terebic Acid

Nomenclature

CAS number: 79-91-4
Tetrahydro-2,2-dimethyl-5-oxo-3-furancarboxylic acid; tetrahydro-2,2-dimethyl-5-oxo-3-furoic acid; terebinic acid; (1-hydroxy-1-methylethyl)succinic acid γ-lactone.
C7H10O4; mol wt 158.15.
C 53.16%, H 6.37%, O 40.47%.

Description and references

Prepared from fumaric or maleic acid: Schenck, Steinmetz, Tetrahedron Letters no. 21, 1 (1960); Lipp et al., Ann. 644, 37 (1961). Prepn of optical isomers: Fredga, C.A. 42, 123g (1948); Delépine, Badoche, Compt. Rend. 235, 1069 (1952).

Chemical structure

Properties

Crystals, mp 174-175°, but begins to volatilize at 100°. d 0.815. Slightly sol in cold water, freely in boiling water or warm alcohol.

Derivative

(+)-Form.

Properties

[α]D25 +13.2° (c = 0.03 in acetone).

Derivative

(-)-Form.

Properties

mp 201-205° (dec). [α]D25 -13.2° (c = 0.03 in acetone).