Sodium Thiosulfate → HCID 90282003, compound

HRID 1497527Notes

Reaction equation

HRID 1497527 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=[O:17])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 67875437HCID 67875437, compound

Product 1

HCID 90282003HCID 90282003, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(benzyloxy)-2-chlorophenyl]ethanol (1.50 g) in dichloromethane (30.0 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.70 g) under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture was added a 1 M aqueous sodium thiosulfate solution, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain [4-(benzyloxy)-2-chlorophenyl]acetaldehyde (1.01 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-785f144335e046d0ba427ec46f7f830c
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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