Bromide ion → 4-Methylpentyn-3-ol

Participants

Reaction Steps

By the procedure of Example 2, the reactant 2-chloro-1-isopropylallyl 4-chloro-2-methyl dithiocarbanilate is prepared by the reaction of 2,3-dichloro-4-methyl-1-pentene and triethylammonium 4-chloro-2-methyldithiocarbanilate. The 2,3-dichloro-4-methyl-1-pentene is prepared by the reaction of isobutyraldehyde with acetylenemagnesium bromide to yield 4-methyl-1-pentyn-3-ol, which is converted to 2-chloro-4-methyl-1-pentene-3-ol by treatment with hydrogen chloride in the presence of mercuric chloride. The required 2,3-dichloro-4-methyl-1-pentene is then obtained by treating 2-chloro-4-methyl-1-pentene-3-ol with phosphorus trichloride.

Provenance & Evidence