Toluene → HCID 131710960, compound

Participants

Reaction Steps

108g (0.5 mole) of 2-norbornyl-4,5-dimethyl phenol, 600 cm3 anhydrous toluene and 11.5g (0.5 mole) sodium are introduced into a three-necked flask supplied with a nitrogen stream. The reaction mixture is refluxed for 4 hours, the solvent is then removed and the residue taken up in 500 cm3 tetrahydrofuran. 39.4 cm3 (0.5 mole) epichlorohydrin are added and the mixture is heated under reflux for 8 hours. One extracts with ether, washes the ethereal phase with water, dries and evaporates the solvent. 123.6g of 1-(2'-norbornyl-4',5'-dimethyl phenoxy) 2,3-epoxypropane are obtained in the form of oil. 27.2g (0.1 mole) of the preceding product are dissolved in 100 cm3 isopropylamine. After 5 days contact, the excess amine is evaporated under reduced pressure and extracted with ether. After washing with water and drying, the ether is evaporated and the residue taken up in chloroform. One precipitates by adding gaseous hydrochloric acid. By crystallisation in methylethyl ketone, 20g of pure product are obtained. M.Pt. 183°-185° C.

Provenance & Evidence