Ethylene Glycol → 7-[4-(1,1-Dimethylethyl)phenyl]-2,3-dihydro-2-(1-methylethyl)-1H-inden-1-one

HRID 2099600Notes

Reaction equation

HRID 2099600 reaction equation
[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[C:7](Cl)[CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])([CH3:3])[CH3:2].[C:15]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O>[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([C:22]3[CH:23]=[CH:24][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:21]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 221729527-Chloro-2,3-dihydro-2-(1-methylethyl)-1H-inden-1-one

Product 1

HCID 231055467-[4-(1,1-Dimethylethyl)phenyl]-2,3-dihydro-2-(1-methylethyl)-1H-inden-1-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

28.0 g of 2-isopropyl-7-chloro-1-indanone, 28.64 g of 4-tert-butylphenylboronic acid, 35.56 g of sodium carbonate, 302 ml of ethylene glycol and 21.6 ml of water are placed in a reaction vessel. The mixture is degassed a number of times by careful application of an oil pump vacuum and subsequent admission of argon, and thus saturated with argon. It is heated to 80° C. and a freshly prepared catalyst solution comprising 60.23 mg of palladium acetate and 1.79 ml of an aqueous TPPTS solution (0.6 molar) in 25 ml of water is then added while stirring vigorously and the reaction mixture is refluxed for 5 hours with further stirring until completely reacted. After cooling to room temperature, 300 ml of water are added. After renewed cooling to room temperature, the ethylene glycol phase is washed 6 times with a total of 900 ml of toluene. The combined toluene phases are washed twice with a total of 250 ml of sodium chloride solution and dried over 150 g of sodium sulfate. Removal of the solvent on a rotary evaporator, drying of the residue and subsequent distillation in an oil pump vacuum gives 40 g (97%) of 2-isopropyl-7-(4′-tert-butylphenyl)-1-indanone as an orange-brown, viscous oil.

Workup

  1. customThe mixture is degassed a number of times by careful application of an oil pump vacuum and subsequent admission of argon
  2. additionis then added
  3. temperaturethe reaction mixture is refluxed for 5 hours
  4. stirringwith further stirring
  5. customuntil completely reacted
  6. temperatureAfter cooling to room temperature
  7. temperatureAfter renewed cooling to room temperature
  8. washthe ethylene glycol phase is washed 6 times with a total of 900 ml of toluene
  9. washThe combined toluene phases are washed twice with a total of 250 ml of sodium chloride solution
  10. dry with materialdried over 150 g of sodium sulfate
  11. customRemoval of the solvent
  12. customon a rotary evaporator
  13. customdrying of the residue and subsequent distillation in an oil pump vacuum

Sources & evidence

ORD record
ord-6a5bf8e9158a42a49c3adfe0e12e0dd8
Source dataset
uspto-grants-2009_08
Patent number
US07569651B2

Reaction notes

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