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

HRID 728046Notes

Reaction equation

HRID 728046 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[CH2:3]1.[OH-].[K+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][CH:5]2[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]2=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium Hydroxide2×HCID 31358Dimedone

Product 1

HCID 11076339HCID 11076339, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
59 °C

Procedure

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 moles) 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 21/2 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 2400 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-chloro- benzyl)-5,5-dimethylcyclohexane-1,3-dione as a white solid, m.pt. 188°-190° C. Yield: 42%.

Workup

  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. custom2 to 3 hours
  7. customup to a temperature of 100° C
  8. temperatureThe mixture was then cooled
  9. filtrationthe solid product filtered off
  10. washwashed with water
  11. customdried in a vacuum oven at 50° C
  12. dissolutionThe crude solid (815 g) was then dissolved in 2400 ml methanol
  13. temperatureat reflux
  14. addition200 ml water added
  15. customto produce a permanent cloudiness
  16. temperatureto cool to room temperature overnight
  17. customThe solid so obtained
  18. filtrationwas filtered
  19. washwashed with about 400 ml cold methanol
  20. customdried in a vacuum oven

Sources & evidence

ORD record
ord-576ded78f3ac4e9ba0502b7ff6f297da
Source dataset
uspto-grants-1991_09
Patent number
US05047426

Reaction notes

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