Triphenylphosphine → Triphenyl{[4-(propan-2-yl)phenyl]methyl}phosphanium chloride

Participants

Reaction Steps

A one liter reactor was obtained, and to this reactor was charged 78.6 g (0.3 mole) of triphenylphosphine, 250 ml of methyl alcohol, and 50.7 g of para-isopropyl-benzyl chloride. The solution was heated to reflux temperature and maintained at reflux for 5 hours. 327.3 g of a 40% solution of para-isopropylbenzyltriphenylphosphonium chloride in methanol was obtained, and to this was added 68.4 g of a 25% solution of sodium methoxide at 10° C., plus 46.5 g of methoxycitronellal also at 10° C. The reactants were allowed to agitate at room temperature approximately 3 hours and thereafter heated to reflux and maintained at reflux for one hour. The reactants were then cooled to room temperature, then charged with 4.5 g of 30% hydrogen peroxide solution and agitated for 1/2 hour. Thereafter the reaction solution was charged with 250 ml of hexane and 100 ml of water and agitated for an additional 1/2 hour. The reaction mixture was allowed to phase separate, and the aqueous phase was decanted off. The organic phase was then charged with 70 ml of methyl alcohol and 30 ml of water and again agitated for 1/2 hour. The aqueous phase was again decanted. The organic phase was then stripped at 110° C., under a full vacuum and nitrogen purge for 2 hours. There was obtained 63.5 g of the intermediate product, 8-methoxy-4,8-dimethyl-1-(4-isopropylphenyl)-1-nonene.

Provenance & Evidence