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

A mixture of 33.4 gm (0.18 mole) of 1,1-dichloro-4-methyl-1-penten-3-one, 40.9 gm (0.20 mole) of aluminum isopropoxide, and 200 ml of isopropanol was heated at reflux for 2 hours. The by-product, acetone, was distilled periodically from the reaction mixture by alternating between reflux and distillation. When the vapor temperature of the distillate reached 82°, the heating was stopped. To the reaction mixture was then added a cold solution of 70 ml of concentrated hydrochloric acid in 350 ml of water. The aqueous mixture was extracted several times with carbon tetrachloride. The combined extracts were dried over magnesium sulfate and filtered. The carbon tetrachloride was evaporated, and the residue was distilled to give 24.9 gm (82% yield) of 1,1-dichloro-3-hydroxy-4-methyl-1-pentene; b.p., 72°/5mm.

1. temperaturewas heated
2. temperatureat reflux for 2 hours
3. distillationThe by-product, acetone, was distilled periodically from the reaction mixture
4. temperaturebetween reflux
5. distillationdistillation
6. customreached 82°
7. additionTo the reaction mixture was then added a cold solution of 70 ml of concentrated hydrochloric acid in 350 ml of water
8. extractionThe aqueous mixture was extracted several times with carbon tetrachloride
9. dry with materialThe combined extracts were dried over magnesium sulfate
10. filtrationfiltered
11. customThe carbon tetrachloride was evaporated
12. distillationthe residue was distilled

ORD record

ord-2c9b020513ac49539967259cea5ff2b9

Source dataset

uspto-grants-1978_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04081488