Dichloromethane → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-benz[f]indan-2-one

HRID 1818648

Reaction equation

HRID 1818648 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)Cl.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C:9]1=[O:17].[CH3:18][CH:19]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH3:20]>CCOCC>[CH3:18][C:19]1([CH3:20])[C:13]2[C:14](=[CH:15][C:16]3[CH2:8][C:9](=[O:17])[CH2:10][C:11]=3[CH:12]=2)[C:23]([CH3:25])([CH3:24])[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 115922,5-Dimethylhexane2×HCID 119832-IndanoneHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 184028485,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-benz[f]indan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

A 1 L 3-neck flask was charged with AlCl3 (80.8 g, 0.606 mol), fitted with a mechanical stirrer, and a 250 mL addition funnel, charged with anhydrous methylene chloride (370 mL). The slurry was cooled to −20° C. and stirred. The addition funnel was then charged (in two portions over the course of the reaction) with a solution of 2-indanone (40.0 g, 0.303 mol) {Note: Aldrich brand 2-indanone was rinsed with ether to remove brown impurities}, 2,5-dichloro, 2,5-dimethylhexane (55.4 g, 0.303 mol) and anhydrous methylene chloride (180 mL). The solution was dripped onto the cold, stirring AlCl3 slurry over the course of 50 min. After stirring for 2.5 h after the addition was complete, a solution of 2,5-dichloro, 2,5-dimethylhexane (13 g, 0.071 mol) and anhydrous methylene chloride (42 mL). After stirring an additional hour, the reaction mixture was poured onto ice (1 L) and treated with ether (500 mL). The organic layer was separated and the aqueous layer extracted with ether (2×200 mL). The combined organic layers were washed with 2.5 M NaCl (aq) (3×75 mL) then water (25 mL) then dried over MgSO4. The dried organic solution was filtered into a 3 L flask and the solvent was slowly removed with a nitrogen blowing over the surface of the solution. The solid that remained was washed with cold pentane and the solids isolated by filtration. The product, a fine crystalline material, was separated manually from a small amount of chunky oily solids that contained product and an impurity. Yield 21 g.

Workup

  1. customfitted with a mechanical stirrer, and a 250 mL addition funnel
  2. additionThe addition funnel was then charged (in two portions
  3. washAldrich brand 2-indanone was rinsed with ether
  4. customto remove brown impurities
  5. stirringAfter stirring for 2.5 h
  6. additionafter the addition
  7. stirringAfter stirring an additional hour
  8. additionthe reaction mixture was poured onto ice (1 L)
  9. customThe organic layer was separated
  10. extractionthe aqueous layer extracted with ether (2×200 mL)
  11. washThe combined organic layers were washed with 2.5 M NaCl (aq) (3×75 mL)
  12. dry with materialwater (25 mL) then dried over MgSO4
  13. filtrationThe dried organic solution was filtered into a 3 L flask
  14. customthe solvent was slowly removed with a nitrogen blowing over the surface of the solution
  15. washThe solid that remained was washed with cold pentane
  16. customthe solids isolated by filtration
  17. customThe product, a fine crystalline material, was separated manually from a small amount of chunky oily solids that

Sources & evidence

ORD record
ord-7219aaacf45b42238eff2059d96c414e
Source dataset
uspto-grants-2009_10
Patent number
US07601666B2

Linked notes

Loading…