Acetone → Methyl 5-(4-chlorobenzyl)-2-formyl-3,4-dimethylbenzoate

HRID 629414Notes

Reaction equation

HRID 629414 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]([CH:17]=C)=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.CC(C)=[O:25].C(#N)C.I([O-])(=O)(=O)=O.[Na+]>[Os]=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:8]([CH3:20])=[C:9]([CH3:19])[C:10]([CH:17]=[O:25])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 118468148Methyl 5-(4-chlorobenzyl)-3,4-dimethyl-2-vinylbenzoate

Product 1

HCID 118468344Methyl 5-(4-chlorobenzyl)-2-formyl-3,4-dimethylbenzoate

Reagents, catalysts & solvents 2

HCID 142273OxoosmiumCatalyst2×HCID 962WaterSolvent

Procedure

To a solution of methyl 5-(4-chlorobenzyl)-3,4-dimethyl-2-vinylbenzoate (0.17 g) in a mixed solvent of acetone (4.00 mL)-acetonitrile (4.00 mL)-water (4.00 mL) were added osmium oxide (fixed catalyst I) (0.07 g) and sodium periodate (0.58 g), and the mixture was stirred overnight at room temperature under argon atmosphere. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.02 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-253b9682fb624f9f8a3e794f55984364
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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