Dimethyl Sulfoxide → 3-Chloronaphthalene-1-carbaldehyde

HRID 1635949Notes

Reaction equation

HRID 1635949 reaction equation
O.O.C[N+]([O-])(C)C.[CH3:8]S(C)=O.[CH2:12]([Cl:14])Cl.C(O[C:18](=[O:20])[CH3:19])C.[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25]C.C(O[C:30](=O)[CH3:31])C>>[Cl:14][C:12]1[CH:8]=[C:19]([CH:18]=[O:20])[C:21]2[C:30]([CH:31]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 198430Trimethylamine oxide dihydrateHCID 21226206Ethyl acetate hexane

Product 1

HCID 186736143-Chloronaphthalene-1-carbaldehydeYield 81%

Procedure

The compound of Preparation 36-2) (3.00 g, 11.7 mmol) and trimethylamine-N-oxide dihydrate(3.90 g, 35.1 mmol) were added to a solvent mixture of DMSO(10 ml) and methylenechloride(5 ml), and the resulting mixture was stirred for 3 hours at room temperature. Ethylacetate(100 ml) was added and the mixture thus obtained was washed three times with aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography(eluent: hexane/ethylacetate=9/1, v/v) to give 1.80 g(9.44 mmol, Yield 81%) of the title compound.

Workup

  1. customthe mixture thus obtained
  2. washwas washed three times with aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6eb947e8c4d1406499b88c7422f7b5e7
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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