Phosphorus oxychloride → 2-(Benzyloxymethyl)-6-chromanecarbaldehyde

HRID 1603872Notes

Reaction equation

HRID 1603872 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][CH2:14][CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:16]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:25]([O-])(=[O:27])C.[Na+]>ClCCl>[CH2:6]([O:13][CH2:14][CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:25]=[O:27])[CH:21]=2)[O:16]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 196063152-(Benzyloxymethyl)chromane

Product 1

HCID 196063282-(Benzyloxymethyl)-6-chromanecarbaldehydeYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorous oxychloride (0.863 ml, 9.26 mmol) was added very slowly and under inert atmosphere on N-methylformanilide (1.14 ml, 9.26 mmol) and the mixture was left under stirring at room temperature for 30 minutes. After that 2-(benzyloxymethyl)chromane (1.569 g, 6.18 mmol) was added stirring at 65° C. for 1.5 h. Subsequently the mixture was diluted with dichloromethane (30 ml), added with a 15% sodium acetate solution (20 ml), the phases were separated and the organic phase was washed successively with a 1M hydrochloric acid solution and a sodium chloride saturated solution. After drying and removing the solvent by evaporation under reduced pressure, a residue was obtained which was purified by flash chromatography through a silica gel column. Eluting with hexane:ethyl acetate, 10:1, 0.921 g of the title product were recovered (53% yield).

Workup

  1. waitthe mixture was left
  2. stirringstirring at 65° C. for 1.5 h
  3. customthe phases were separated
  4. washthe organic phase was washed successively with a 1M hydrochloric acid solution
  5. customAfter drying
  6. customremoving the solvent
  7. customby evaporation under reduced pressure
  8. customa residue was obtained which
  9. customwas purified by flash chromatography through a silica gel column
  10. washEluting with hexane
  11. customethyl acetate, 10:1, 0.921 g of the title product were recovered (53% yield)

Sources & evidence

ORD record
ord-97ffed544321446daab1e02edea57de1
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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