Sodium periodate → 2-(1-Phenylcyclohexyl)acetaldehyde

HRID 714250Notes

Reaction equation

HRID 714250 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.O=[Os](=O)(=O)=O.CC(O)(C)C>[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 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 30318Osmium TetroxideSolvent

Procedure

To a solution of (1-allylcyclohexyl)benzene (210 mg, 1.048 mmol) in THF (5 mL) were 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. The mixture was stirred at room temperature for 18 hrs. The mixture was extracted with EtOAc and washed with brine. The combined aqueous layers were back extracted with EtOAc and combined. The resulting material was dried over Na2SO4 and evaporated to give an oily residue. 1H NMR (400 MHz, CDCl3) δ ppm 9.36 (2 H, t, J=3.08 Hz), 7.18-7.42 (5 H, m), 2.58 (2 H, d, J=3.30 Hz), 1.34-1.81 (10 H, m).

Workup

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

Sources & evidence

ORD record
ord-44576368f4d54802988950d082a55df7
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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