Behavior of the lactone of cis-S-hydroxycyclohexanecarboxylic acid in concentrated sulfuric add. Fifteen grams of the lactone of cis-3-hydroxycyclohexanecarboxylic acid was dissolved in 50 ml. of coned, sulfuric acid and allowed to stand at room temperature for 48 hr. At the end of this period the opaque brown mixture was poured into water and continuously extracted with ether. The extracts were dried, evaporated, and the product fractionally distilled. The main fraction, b.p. 115°( 8 mm.) weighing 4.2 g. (28%) was obtained and proved to be the lactone of «s-4-hydroxycyclohexanecarboxylic acid. One crystallization from ether-pentane yielded 3.3 g. of lactone melting over a range to 124°. Crystallization of a small sample gave material of m.p. 127-128°, (lit.lsm.p. 126-128°). The infrared spectrum was identical with that of an authentic sample of cw-4-hydroxycyclohexanecarboxylic acid lactone.
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