Ethylene Glycol → 4-(4-tert-Butyl-phenyl)-indan-1-one

HRID 1169168Notes

Reaction equation

HRID 1169168 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[C:12]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C(O)CO.C(=O)([O-])[O-].[Na+].[Na+]>O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+]>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 113326814-chloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 229905194-(4-tert-Butyl-phenyl)-indan-1-oneYield 96%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)CatalystHCID 962WaterSolvent2×

Procedure

14.0 g (84 mmol) of 4-chloroindanone, 32.9 g (185 mmol) of 4-tert-butylphenylboronic acid, 230 ml of ethylene glycol and 38 ml of water together with 19.6 g of sodium carbonate are placed in a reaction vessel and degassed three times. A solution of 94 mg (0.42 mmol) of Pd(OAc)2 and 2.1 ml (1.26 mmol) of TPPTS in 2 ml of water is subsequently added. The resulting reaction mixture is refluxed for 5 hours. After cooling, it is extracted three times with toluene and the combined organic phases are washed with saturated NaCl solution. After drying over magnesium sulfate, the solvent is removed in an oil pump vacuum. 21.3 g (96%) of the desired product are isolated.

Workup

  1. customdegassed three times
  2. customThe resulting reaction mixture
  3. temperatureis refluxed for 5 hours
  4. temperatureAfter cooling
  5. extractionit is extracted three times with toluene
  6. washthe combined organic phases are washed with saturated NaCl solution
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent is removed in an oil pump vacuum

Sources & evidence

ORD record
ord-e21b2a6e20df4519acd79ce1ea91338d
Source dataset
uspto-grants-2003_09
Patent number
US06627764B1

Reaction notes

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