Sodium Thiosulfate → (2-Fluorophenyl)acetaldehyde

HRID 1665440Notes

Reaction equation

HRID 1665440 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]=[O:10]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Product 1

HCID 17770161(2-Fluorophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Fluorophenyl)ethanol (Ald, 1.0 g) was dissolved in dichloromethane (KANTO, 20 mL) under nitrogen atmosphere and added with Dess-Martin reagent (Alfa Aesar, 3.64 g), followed by stirring at room temperature for 3 hours. Saturated sodium thiosulfate solution was added to the reaction mixture and then extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate solution and brine, and then dried over anhydrous magnesium sulfate. The reaction solution was concentrated under reduced pressure to obtain the target compound as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88e81f3230f94c089bf36e2c1fe29e07
Source dataset
uspto-grants-2011_10
Patent number
US08039514B2

Reaction notes

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