Triacetoxyperiodinane → 3-Methyl-2-nitrobenzaldehyde

HRID 1174352Notes

Reaction equation

HRID 1174352 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 5619893-Methyl-2-nitrobenzenemethanol

Product 1

HCID 135735673-Methyl-2-nitrobenzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-methyl-2-nitrobenzyl alcohol (0.4 g, 2.4 mmol) in acetonitrile (8 mL) was treated with Dess-Martin reagent (1.11 g, 2.63 mmol) at 25° C. for 16 h. The mixture was quenched with sodium bicarbonate/sodium thiosulfate (1:1, 15 mL), and the mixture was extracted with dichloromethane, the organic layer separated, washed with brine, dried over sodium sulfate, filtered, and the solvents were evaporated to give the crude title compound (0.387 g, 98%).

Workup

  1. customThe mixture was quenched with sodium bicarbonate/sodium thiosulfate (1:1, 15 mL)
  2. extractionthe mixture was extracted with dichloromethane
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were evaporated

Sources & evidence

ORD record
ord-67b24b1500684ef7803136e998954f78
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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