Triacetoxyperiodinane → 2-Butoxy-4-formyl-benzoic Acid Methyl Ester

HRID 424804Notes

Reaction equation

HRID 424804 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16].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:17])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 574433312-Butoxy-4-hydroxymethyl-benzoic acid methyl ester

Product 1

HCID 574433192-Butoxy-4-formyl-benzoic Acid Methyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 2-butoxy-4-hydroxymethyl-benzoic acid methyl ester (0.270 g, 1.13 mmol) in methylene chloride (10 mL) are added sodium bicarbonate (0.14 g, 1.7 mmol) and Dess-Martin periodinane (0.58 g, 1.4 mmol) sequentially. The reaction mixture is stirred at room temperature for 1.0 h and quenched with water (10 mL). The reaction mixture is partitioned between CH2Cl2 (30 mL) and water (20 mL). The organic phase is washed with brine (20 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 a syrup (240 mg, 90%). LC-ES/MS: 237.3 (M+1).

Workup

  1. customquenched with water (10 mL)
  2. customThe reaction mixture is partitioned between CH2Cl2 (30 mL) and water (20 mL)
  3. washThe organic phase is washed with brine (20 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-99949e92b5c44cb09b689d2a1661b8de
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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