Sodium Thiosulfate → 4-(2-Oxoethyl)benzonitrile

HRID 1466121Notes

Reaction equation

HRID 1466121 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:1]=[CH:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 125916704-(2-Oxoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-Hydroxyethyl)benzonitrile (0.38 g, 2.6 mmol) in DCM (5 mL) was added Dess-Martin reagent (1.7 g, 3.9 mmol). The mixture was allowed to stir at RT for 1 hour. TLC showed no starting material at that point. The reaction was diluted with DCM, worked up with Na2S2O3, washed with sodium bicarbonate, dried over sodium sulfate, and concentrated. The crude 4-(2-Oxoethyl)benzonitrile was used in the next step without further purification.

Workup

  1. washwashed with sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude 4-(2-Oxoethyl)benzonitrile was used in the next step without further purification

Sources & evidence

ORD record
ord-c0831ae978304cd5b3ab5a409b403213
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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