Ozone → Methyl 2-formyl-6-methoxybenzoate

HRID 1476828Notes

Reaction equation

HRID 1476828 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]=C)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].[O:15]=[O+][O-]>C(Cl)Cl>[CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:15]

Participants

4

Reactant 2

HCID 24823OzoneHCID 15953550Methyl 2-ethenyl-6-methoxybenzoate

Product 1

HCID 12730360Methyl 2-formyl-6-methoxybenzoateYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of methyl 2-methoxy-6-vinylbenzoate (22 g, 0.11 mol) in anhydrous DCM (400 mL) was bubbled O3 at −78° C. over a 30 minute period. Next, nitrogen gas was bubbled into the solution until it turned colorless. Dimethylsulfane (20 mL) was added dropwise and the resulting mixture was warmed to RT and stirred for 2 hours. The mixture was washed with water (30 mL) and the aqueous layer was extracted with DCM (3×100 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography eluting with a gradient of EtOAc (0-90%) and PE to give the title compound (11.8 g, 53.6%). 1H NMR (400 MHz, CDCl3) δ ppm 9.97 (s, 1H), 7.56 (t, J=8.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 3.98 (s, 3H), 3.90 (s, 3H).

Workup

  1. customNext, nitrogen gas was bubbled into the solution until it
  2. additionDimethylsulfane (20 mL) was added dropwise
  3. washThe mixture was washed with water (30 mL)
  4. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluting with a gradient of EtOAc (0-90%) and PE

Sources & evidence

ORD record
ord-08dbdcd7961f4bf9a0b16e086dbcea5c
Source dataset
uspto-grants-2016_08
Patent number
US09402841B2

Reaction notes

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