2724. Cyclohexanecarboxylic Acid

Nomenclature

CAS number: 98-89-5
Hexahydrobenzoic acid.
C7H12O2; mol wt 128.17.
C 65.60%, H 9.44%, O 24.97%.

Description and references

Prepn from anisic acid: Lumsden, J. Chem. Soc. 87, 90 (1905); from 2-chlorocycloheptanone: Gutsche, J. Am. Chem. Soc. 71, 3513 (1949); by carbonation of cyclohexylmagnesium chloride: Wagner, Moore, ibid. 72, 974 (1950); from cyclohexane + KI + active Ni: Reppe et al., Ann. 582, 38 (1953); by oxidation of cycloheptanone: Payne, Smith, J. Org. Chem. 22, 1680 (1957); from cyclohexane + HCOOH or CO2: McKursick et al., J. Am. Chem. Soc. 82, 723 (1960); McKursick, US 2940913 (1960 to du Pont).

Chemical structure

Properties

Liquid. bp 232.5°; bp20 131°; bp8 110°; bp<1 63-67°. Crystallizes, on cooling, in monoclinic prisms, mp 29°. Odorless but when liquid or in soln has a valerian odor. d415 1.0480. nD20 1.4530. Soly in 100 g water at 15°: 0.201 g. Sol in most organic solvents.

Derivative

Methyl ester.
C8H14O2; mol wt 142.20.
C 67.57%, H 9.92%, O 22.50%.

Properties

Fragrant liq, bp 183°. d415 0.9954.

Use

Solubilizer for vulcanized rubber; clarifier for mineral oil; in insecticide formulations.