Natural acetylenes. Part XXVIII. C17-polyacetylenic alcohols from the Umbellifer Daucus carota L. (carrot) : alkylation of benzene by acetylenyl(vinyl)carbinols in the presence of toluene-p-sulphonic acid

Abstract

Three acetylenic compounds, the known alcohol (A; X = OH, Y = H) and diol (A; X = Y = OH) and the new monoacetate (A; X = OAc, Y = OH) have been isolated from the roots of the common carrot, Daucus carota L. H₂CCH·CHX·[CC]₂·CHY·CH [graphic omitted] CH·[CH₂]₆Me (A) When refluxed with toluene-p-sulphonic acid in benzene, the alcohol and synthetic oct-1-ene-4,6-diyn-3-ol rearranged to the expected primary alcohols (and tosylates) but in addition yielded benzenoid hydrocarbons of the type PhCH₂·CHCH·[CC]₂R, arising from attack on the solvent.