cicloxilic acid

Originator

Plecton ,Guidotti, Italy ,1975

Definition

ChEBI: (1S,2R)-cicloxilic acid is a 2-hydroxy-2-phenylcyclohexanecarboxylic acid that has (1S,2R)-stereoconfiguration. It is an enantiomer of a (1R,2S)-cicloxilic acid.

Manufacturing Process

25 g of 2-hydroxy-methyl-cyclohexanone, diluted in 20 cc of ether, were dropped into a vessel containing an ether suspension of phenyl-magnesiumbromide (prepared from 19.6 g of magnesium and 128 g of bromobenzene in 300 cc of ether according to usual techniques by stirring and external icecooling). The mixture was stirred for some time, then the magnesium compound was decomposed by pouring it carefully into water and ice; the magnesium hydroxide was dissolved in 50 cc of a saturated solution of ammonium chloride, the ether portion was separated and the aqueous portion extracted with further ether.
Collected and dried ether extracts were evaporated and the residue vacuum distilled yielded 15 g of a thick oil of boiling point at 0.1 to 0.2 mm Hg 127°C to 135°C.
This product crystallized by dissolving in ether and reprecipitation with petroleum ether yielded 7 g of 1-phenyl-2-hydroxy-ethylene-cyclohexan-1-ol, melting point (Kofler) 81°C to 83°C.
The thus obtained product was dried and finely powdered, and then suspended in 1.4 liters of an aqueous solution of 14 g of KMnO4 and 7 g of N2CO3, and the suspension was thoroughly stirred for one day.
After filtering off the MnO2, thus formed, a small amount of Na2SO3 was added until the violet coloration disappeared; MnO2 was filtered again and the alkaline solution was acidified with concentrated HCl.
After one day standing in a refrigerator, the product was filtered and washed with water, thus yielding 5 g of 2-phenyl-2-hydroxy-cyclohexane-carboxylic acid, melting point (Kofler) 143°C to 145°C.

Therapeutic Function

Choleretic