1-Chloro-4-(chloromethyl)benzene → HCID 11076339, compound

Temperature

59 °C

449 g (3.21 mols) dimedone (5,5-dimethylcyclohexane-1,3-dione) were added to a solution of aqueous potassium hydroxide comprising 166 g of 85% potassium hydroxide (2.52 mols) in 700 ml of water. The mixture was then warmed and a clear orange solution was obtained at 47° C. The solution was then heated to 59° C. and 544 g (3.21 mols) molten 4-chlorobenzyl chloride were added over a period of 1 hour with further heating to 85° C. Heating was continued for a further 2.5 to 3 hours up to a temperature of 100° C. The mixture was then cooled, the solid product filtered off, washed with water and dried in a vacuum oven at 50° C. The crude solid (815 g) was then dissolved in 2,400 ml methanol at reflux and 200 ml water added to produce a permanent cloudiness. The mixture was then allowed to cool to room temperature overnight with stirring. The solid so obtained was filtered, washed with about 400 ml cold methanol and dried in a vacuum oven to produce 340 g 2-(4-chlorobenzyl)-5,5-dimethylcyclohexane-1,3-dione as a white solid, m.pt. 188°-190° C. Yield: 42%.

1. temperatureThe mixture was then warmed
2. customa clear orange solution was obtained at 47° C
3. additionwere added over a period of 1 hour
4. temperaturewith further heating to 85° C
5. temperatureHeating
6. temperatureThe mixture was then cooled
7. filtrationthe solid product filtered off
8. washwashed with water
9. customdried in a vacuum oven at 50° C
10. dissolutionThe crude solid (815 g) was then dissolved in 2,400 ml methanol
11. temperatureat reflux
12. addition200 ml water added
13. customto produce a permanent cloudiness
14. temperatureto cool to room temperature overnight
15. customThe solid so obtained
16. filtrationwas filtered
17. washwashed with about 400 ml cold methanol
18. customdried in a vacuum oven

ORD record

ord-6fb1466f1fec4b78ae1ec3d1149214dd

Source dataset

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05262543