Sodium Thiosulfate → 2-(3-chlorophenyl)acetaldehyde

HRID 1620987Notes

Reaction equation

HRID 1620987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 78856m-Chlorophenethylic alcoholHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Product 1

HCID 115791652-(3-chlorophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of Example 86A (5.73 g, 36.5 mmol) and Dess-Martin periodinane (18.6 g, 43.8 mmol) in 200 mL of dichloromethane was stirred under N2 atmosphere for 4 hours at room temperature. Then saturated NaHCO3 (500 mL) and Na2S2O3 (100 mL) was added with stirring for another 30 minutes. The mixture was extracted with dichloromethane (3×300 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The crude product was purified by distillation under reduced pressure.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×300 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationThe crude product was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-580666ad38aa4e8b8abaf4af38a0133e
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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