Sodium Thiosulfate → 2-(2,6-Dichlorophenyl)acetaldehyde

HRID 474302Notes

Reaction equation

HRID 474302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][OH:11].C(OI1(OC(=O)C)(OC(=O)C)C2C(=CC=CC=2)C(=O)O1)(=O)C.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH:10]=[O:11]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 27341002-(2,6-Dichlorophenyl)ethanol

Product 1

HCID 122635642-(2,6-Dichlorophenyl)acetaldehydeYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichlorophenylethylalcohol (2.0 g, 10.5 mmol) and CH2Cl2 (50 mL) was added acetic acid 1,1-diacetoxy-3-oxo-1λ5-ioda-2-oxa-indan-1-yl ester (Dess-Martin periodinane; 4.9 g, 11.5 mmol) at rt. After 30 min. the mixture was diluted with satd. aq. NaHCO3 (10 mL) and satd. aq. Na2S2O3 (10 mL) and was stirred at rt for 1 h. The mixture was extracted with CH2Cl2 (3×15 mL) and the combined organic layers were dried (MgSO4), concentrated, and purified by FCC to afford a colorless solid (1.4 g, 70%). 1H NMR (CDCl3): 9.76 (dd, J=2.24, 1.12 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.25-7.20 (m, 1H), 4.14 (d, J=0.93 Hz, 1H).

Workup

  1. additionAfter 30 min. the mixture was diluted with satd
  2. extractionThe mixture was extracted with CH2Cl2 (3×15 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by FCC

Sources & evidence

ORD record
ord-f6b1358ed37945918514a388cf7c4e8e
Source dataset
uspto-grants-2014_01
Patent number
US08637527B2

Reaction notes

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