Sodium Thiosulfate → 2-(3-(Trifluoromethyl)phenyl)acetaldehyde

HRID 1485070Notes

Reaction equation

HRID 1485070 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][OH:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH2:6][CH:7]=[O:8])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 959263-(Trifluoromethyl)phenethylic alcoholHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Product 1

HCID 212463392-(3-(Trifluoromethyl)phenyl)acetaldehydeYield 60.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-(trifluoromethyl)phenethyl alcohol (2.00 g) in chloroform (50.0 mL), Dess-Martin periodinane (4.70 g) was added under cooling with ice. After being brought to room temperature, the reaction mixture was stirred for an hour. Subsequently, a saturated aqueous solution of sodium hydrogencarbonate (25.0 mL) and a saturated aqueous solution of sodium thiosulfate (25.0 mL) were added and the mixture was vigorously stirred for an hour. After phase separation, the organic layer was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-85:15) to give the titled compound as a pale yellow oil (1.19 g).

Workup

  1. temperatureunder cooling with ice
  2. customAfter being brought to room temperature
  3. stirringthe mixture was vigorously stirred for an hour
  4. customAfter phase separation
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customthe desiccant was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-85:15)

Sources & evidence

ORD record
ord-5499289300934ec392cbbf0a12edf137
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

Loading…