Linalool is a fragrance compound that gives floral/spicy notes. I read about this reaction on P 269 of 'Perfumery and flavoring synthetics' by Bedoukian (1986). A synthesis of linalool is carried out by a little known step that treats methyl heptenone with sodium acetylide. This is a way to functionalize at a carbonyl, kind of like a grignard reaction. It says:
"Finally, linalool (I) was synthesized by Ruzicka and Fornasir through a very interesting series of reactions. Employing a reaction discovered earlier by Nef, they condensed methyl heptenone (V) with sodium acetylide and obtained dehydrolinalool (VI). The acetylinic linkage was reduced with sodium to the ethylenic linkage to give dl-linalool (I)."
"Finally, linalool (I) was synthesized by Ruzicka and Fornasir through a very interesting series of reactions. Employing a reaction discovered earlier by Nef, they condensed methyl heptenone (V) with sodium acetylide and obtained dehydrolinalool (VI). The acetylinic linkage was reduced with sodium to the ethylenic linkage to give dl-linalool (I)."
