Aluminum isopropoxide → 1,1-Dichloro-4-methylpent-1-en-3-ol

Participants

Reaction Steps

The reaction vessel containing the aluminum isopropoxide was fitted with a condenser, and 1737 gm (10.60 moles) of 1,1-dichloro-4-methyl-1-penten-3-one was added. The reaction mixture was heated to reflux, and the evolved acetone was removed by distillation over a 19.25 hour period. The isopropanol was then removed by distillation, and the residue was separated into two portions of 1100 ml and 1900 ml respectively. The 1100 ml portion was hydrolyzed in 3000 ml of aqueous hydrochloric acid and then washed three times with 900 ml of benzene. For the 1900 ml portion, 5100 ml of aqueous hydrochloric acid and 1500 ml of benzene were used. The benzene washes were combined and washed with 4000 ml of water. The organic layer was separated and dried over magnesium sulfate. Most of the benzene was removed by distillation under atmospheric pressure. The residue was filtered, and the last trace of solvent was removed by distillation under reduced pressure. The residue was distilled under reduced pressure to give 1698 gm (94.8% yield) of 1,1-dichloro-3-hydroxy-4-methyl-1-pentene; b.p., 67°-83°/4-7mm.

Provenance & Evidence