Sodium Thiosulfate → 2-Naphthaleneacetaldehyde

HRID 1165414Notes

Reaction equation

HRID 1165414 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(=O)(O)[O-].[Na+]>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][CH:2]=[O:1]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 738772-NaphthaleneethanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 108991132-Naphthaleneacetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(2-hydroxyethyl)naphthalene (50 mmol, 8.60 g) in dichloromethane (400 ml) at 0° C. was added Dess-Martin periodinate (50 mmol, 21.2 g) [J. Org. Chem. 48 4155 (1983)] in one portion. The solution was stirred at 0° C. for 10 mintes and at room temperature for 45 minutes. The reaction mixture was diluted with dichloromethane (400 ml) and sodium bicarbonate (1.0 L) containing sodium thiosulfate (55 g). The mixture was shaken for five minutes and the layers separated. The aqueous phase was extracted with dichloromethane (800 ml) and the combined organic solutions were washed with saturated sodium bicarbonate (800 ml), dried over sodium sulfate and concentrated in vacuo to provide naphthalen-2-ylacetaldehyde.

Workup

  1. stirringThe mixture was shaken for five minutes
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with dichloromethane (800 ml)
  4. washthe combined organic solutions were washed with saturated sodium bicarbonate (800 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2feb31ea85b149459d7ea417e4cca3aa
Source dataset
uspto-grants-1990_03
Patent number
US04910019

Reaction notes

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