GB561508A - Manufacture of tri-p-anisyl-chloroethylene - Google Patents

Abstract

Tri-p-anisyl-chloroethylene is prepared by treating tri-p-anisyl-ethylene or tri-p-anisylethanol dissolved in an organic solvent with an approximately equimolecular proportion of chlorine. A very slight excess of chlorine, such as 2-5 per cent, may be used, but beyond this amount more highly chlorinated products are formed. Solvents mentioned include carbon tetrachloride, glacial acetic acid, chlorobenzene and nitrobenzene. In examples: (1) tri-p-anisyl ethylene in glacial acetic acid solution is treated with a solution of chlorine in glacial acetic acid at 20-30 DEG C. with external cooling if necessary, and allowed to stand at room temperature for 1/2 hour. A final reflux removes hydrogen chloride and the product is precipitated by the addition of water; (2) a nitrobenzene solution of tri-p-anisyl ethylene is treated with a nitrobenzene solution of chlorine and worked up as in example (1); (3) chlorine gas is passed through an ether solution of tri-p-anisyl-ethylene and the product worked up as before; (4) a carbon tetrachloride solution of tri-p-anisyl-ethylene is treated with a carbon tetrachloride solution of chlorine; (5) a carbon tetrachloride solution of tri-p-anisyl ethanol is treated with a carbon tetrachloride solution of chlorine below 25 DEG C.; (6) a nitrobenzene solution of tri-p-anisyl ethanol is treated with a nitrobenzene solution of chlorine. In each of the above examples the product is tri-p-anisyl chloroethylene. Specifications 518,149, 549,200 and 559,374 are referred to.