Methanol → Methyl 3-(2-formylphenyl)propionate

HRID 2211372Notes

Reaction equation

HRID 2211372 reaction equation
[CH3:1][O:2][C:3]1[CH2:4][CH2:5][C:6]2[C:11](C=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C(=O)(O)[O-:14].[Na+].[CH3:18][OH:19]>ClCCl>[CH:18]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:14])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 11105653Naphthalene, 1,2-dihydro-3-methoxy-

Product 1

HCID 12241421Methyl 3-(2-formylphenyl)propionateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4.5 g of 3-methoxy-1,2-dihydronaphthalene, 1 g of sodium bicarbonate, 20 mL of methanol and 80 mL of dichloromethane was stirred and cooled in a dry ice-acetone bath. A rapid stream of ozone was bubbled into the suspension until a persistent blue coloration was visible. The mixture was flushed with nitrogen and 3.5 mL of methyl sulfide was added. The mixture was stirred in an ice-acetone bath for 1 hour and then 2 hours at room temperature. The organic solution was washed with water, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether to provide 5.0 g (90%) of the desired title intermediate. NMR.

Workup

  1. temperaturecooled in a dry ice-acetone bath
  2. customA rapid stream of ozone was bubbled into the suspension until a persistent blue coloration
  3. customThe mixture was flushed with nitrogen and 3.5 mL of methyl sulfide
  4. additionwas added
  5. stirringThe mixture was stirred in an ice-acetone bath for 1 hour
  6. custom2 hours
  7. customat room temperature
  8. washThe organic solution was washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether

Sources & evidence

ORD record
ord-60a039416e1a40ab85390621af2e99ca
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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