Water → 4-(2-Phenylpropan-2-yl)benzaldehyde

HRID 1025537

Reaction equation

HRID 1025537 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].N12CC3CC(CC(C3)C1)C2.O.[C:27]([O-])([O-])=[O:28].[K+].[K+]>C(O)(C(F)(F)F)=O>[C:10]1([C:2]([C:4]2[CH:9]=[CH:8][C:7]([CH:27]=[O:28])=[CH:6][CH:5]=2)([CH3:1])[CH3:3])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13065DimethyldiphenylmethaneHCID 1361061-Azatricyclo(3.3.1.13,7)decane

Product 1

HCID 185094134-(2-Phenylpropan-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of propane-2,2-diyldibenzene (3.93 g, 20 mmol) and 1-aza-tricyclo[3.3.1.1*3,7*]decane (2.80 g, 20 mmol) in TFA (35 mL) was heated at 100° C. for 16 h. The reaction mixture was allowed to cool to RT, poured onto cold water and made alkaline (pH=9) with solid K2CO3. The aqueous solution was extracted with Et2O (3×250 mL) and the separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, petroleum ether:EtOAc 95:5) affording the title compound (3.47 g, 15.46 mmol).

Workup

  1. temperatureto cool to RT
  2. extractionThe aqueous solution was extracted with Et2O (3×250 mL)
  3. dry with materialthe separated organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel, petroleum ether:EtOAc 95:5)

Sources & evidence

ORD record
ord-ea912622638f403596548aa4bad79d7d
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Linked notes

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