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

Participants

Reaction Steps

22.9 g (0.109 mol) of 4-Bromo-indan-1-one, 23.18 g (0.130 mol) of 4-tert-butylphenylboronic acid, 23.0 g (0.217 mol) sodium carbonate, 67 ml water and 357 ml of ethylene glycol are placed into a round bottom flask with reflux condenser and stirrer. The flask is evacuated and refilled with argon three times to remove any oxygen. 49 mg (0.22 mmol) of Palladium(II) acetate and 1.4 ml (0.87 mmol) of a 0.6 M solution of NaTPPTS (tris-sodiumtriphenylphosphine-3,3′,3″-trisulfonate) are premixed in 2 ml of water and added to the reaction mixture which is subsequently heated to reflux. The progress of the reaction is monitored via TLC. Complete conversion should be achieved within 3.5 to 5 hours. The mixture is cooled to room temperature and water and toluene are added until two clearly discernible phases form. The layers are separated and the water phase is extracted three times with toluene. The combined organic layers are washed twice with a saturated sodium chloride solution, dried over anhydrous magnesium sulphate and the solvent is removed in a vacuum to yield an oily product. The GC-determined purity of the crude product is 92%. Pure product can be obtained by treating the oily residue with 35 ml of ethanol at room temperature. Solid 4-(4-tert-Butyl-phenyl)-indan-1-one precipitates and is filtered of. The filtrate still contains significant amounts of product which can be isolated by evaporating the filtrate to dryness mixing it with 50 ml of heptane and storing the mixture at −30° C. over night. The filtrate is filtered off, washed with two portions of cold (30° C.) heptane and dried in a vacuum (Combined yield: 23.71 g, 82%).

Provenance & Evidence