Triacetoxyperiodinane → Methyl 4-formyl-2-methylbenzoate

HRID 424801Notes

Reaction equation

HRID 424801 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[CH3:12].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[CH3:12]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 23021531Methyl 4-(hydroxymethyl)-2-methylbenzoate

Product 1

HCID 20134203Methyl 4-formyl-2-methylbenzoateYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-hydroxymethyl-2-methyl-benzoic acid methyl ester (0.49 g, 2.7 mmol) in methylene chloride (8.0 mL) is added sodium bicarbonate (0.46 g, 5.4 mmol) and Dess-Martin periodinane (0.14 g, 3.3 mmol) sequentially. The reaction mixture is stirred at room temperature for 1.0 h and quenched with water (2.0 mL). The mixture is partitioned between CH2Cl2 (30 mL) and water (30 mL). The organic phase is washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to give the title compound as syrup (0.35 g, 72%). 1HNMR (CDCl3) (ppm): 2.6 (3H, s), 3.85 (3H, s), 7.65-8.0 (3H, m), 10.0 (1H, s).

Workup

  1. customquenched with water (2.0 mL)
  2. customThe mixture is partitioned between CH2Cl2 (30 mL) and water (30 mL)
  3. washThe organic phase is washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4ba6e074878e40c392df78981eb4974b
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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