Sodium periodate → 2-(1-Phenylcyclohexyl)acetaldehyde

HRID 71246Notes

Reaction equation

HRID 71246 reaction equation
[CH2:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:17].[Na+]>C1COCC1.O.CC(O)(C)C.O=[Os](=O)(=O)=O>[C:10]1([C:4]2([CH2:1][CH:2]=[O:17])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 86688202(1-Allylcyclohexyl)benzene

Product 1

HCID 866882032-(1-Phenylcyclohexyl)acetaldehyde

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1-allylcyclohexyl)benzene (210 mg, 1.048 mmol) in THF (5 mL) was added a solution of sodium periodate (538 mg, 2.52 mmol) in water (5.00 mL), and 0.105 ml of 2.5% OsO4 in t-BuOH, and the mixture was stirred at room temp for 18 hrs. It was extracted with EtOAc and washed with brine. The combined aqueous layers were back extracted with EtOAc and combined. Dried over Na2SO4 and evaporated to give an oily residue. 1H NMR (400 MHz, CCl3D) δ ppm 9.36 (2H, t, J=3.08 Hz), 7.18-7.42 (5H, m), 2.58 (2H, d, J=3.30 Hz), 1.34-1.81 (10H, m).

Workup

  1. extractionIt was extracted with EtOAc
  2. washwashed with brine
  3. extractionThe combined aqueous layers were back extracted with EtOAc
  4. dry with materialDried over Na2SO4
  5. customevaporated
  6. customto give an oily residue

Sources & evidence

ORD record
ord-9cc45e286dce47b5a83afd6294b57958
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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