Sodium Chloride → 1-Chloro-3-(3,4-methylenedioxy-phenoxy)-propane

HRID 1168987Notes

Reaction equation

HRID 1168987 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[H-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16]I.[Na+].[Cl-]>CN(C=O)C.O>[O:2]1[C:3]2[CH:9]=[CH:8][C:7]([O:10][CH2:16][CH2:15][CH2:14][Cl:13])=[CH:6][C:4]=2[O:5][CH2:1]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 68289SesamolHCID 813631-Chloro-3-iodopropane

Product 1

HCID 198038641-Chloro-3-(3,4-methylenedioxy-phenoxy)-propane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of sesamol (2.00 g, 14.48 mmol) in DMF (15 mL) was slowly added over 5 min to a cold (0-5° C.), stirring slurry of sodium hydride (0.65 g of an 80% dispersion in mineral oil, 21.67 mmol) in DMF (10 mL). The mixture was allowed to warm to ambient temperature and further stirred for 1 h. To this slurry was added drop-wise over 5 min, 1-chloro-3-iodopropane (3.55 g, 1 7.37 mmol), and the resulting brown mixture was stirred at ambient temperature for 4 h. Cold water (25 mL) was carefully added, followed by saturated NaCl solution (25 mL). The resulting mixture was extracted with ether (4×50 mL). The combined ether extracts were dried (MgSO4), filtered, concentrated by rotary evaporation to a residue that was dried briefly under high vacuum producing a brown oil.

Workup

  1. additionTo this slurry was added drop-wise over 5 min
  2. extractionThe resulting mixture was extracted with ether (4×50 mL)
  3. dry with materialThe combined ether extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation to a residue that
  6. customwas dried briefly under high vacuum
  7. customproducing a brown oil

Sources & evidence

ORD record
ord-06d7d12ddf6548ffa1f059d6d3118db1
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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