Triacetoxyperiodinane → Methyl 4-formyl-2-methylbenzoate

HRID 2261797Notes

Reaction equation

HRID 2261797 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) are added sodium bicarbonate (0.46 g, 5.4 mmol) and Dess-Martin periodinane (0.14 g, 3.3 mmol) sequentially. The mixture is stirred at room temperature for 1.0 h and is 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 afford 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. customis quenched 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-34060d45112543ac9be19adf3c5c2267
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…