Hydrochloric Acid → Z-4-(3-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol

Reaction equation

[Cl:1][CH:2]=[CH:3][CH2:4][C:5]1[C:18]([F:19])=[C:17]([F:20])[C:8]([CH2:9][O:10]C2CCCCO2)=[C:7]([F:21])[C:6]=1[F:22].Cl>CO.O>[Cl:1]/[CH:2]=[CH:3]\[CH2:4][C:5]1[C:6]([F:22])=[C:7]([F:21])[C:8]([CH2:9][OH:10])=[C:17]([F:20])[C:18]=1[F:19]

Participants

Procedure

The tetrahydropyranyl ether prepared in stage (ii) was dissolved in methanol (30 cm3), and to the stirred solution was added a catalytic amount of concentrated hydrochloric acid. After stirring for two hours, the reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed and dried, and the solvent evaporated under reduced pressure to give Z-4-(3-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyl alcohol (0.6 g) as a colourless oil, which solidified on standing.