Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 54091266, compound

Participants

Reaction Steps

A mixture of 4.5 g of the said butyraldehyde and 5.48 g of carbethoxy methylene triphenyl phosphorane in 100 ml of toluene was refluxed under an inert atmosphere with stirring for 17 hours and the toluene was then evaporated. The residue was saponified with 30 ml of 2 N sodium hydroxide and 50 ml of methanol at 75°-80° C. and the methanol was then removed. Water was added to the mixture which was then washed with ether containing 20% of methylene chloride, was treated with activated carbon and filtered. The filtrate was acidified with concentrated hydrochloric acid and was extracted with ether. The ether extracts were treated with activated carbon, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 95:5 methylene chloride-methanol mixture. The product was crystallized from isopropyl ether to obtain 2.015 g of 6-[3'-(4-chlorobenzyl)-2'-methylphenyl]-hex-2-enoic acid melting at 115° C.

Provenance & Evidence