3-Chloro-1-propanol → HCID 18755397, compound

HRID 843449Notes

Reaction equation

HRID 843449 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[O:10][CH3:11].[Cl:12][CH2:13][CH2:14][CH2:15][OH:16].[H-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:12][CH2:13][CH2:14][CH2:15][O:16][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 123133-Chloro-1-propanolHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 187554391-(Chloromethyl)-4-fluoro-2-methoxybenzene

Product 1

HCID 18755397HCID 18755397, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 0.36 g (2.06 mmol) of 1-chloromethyl-4-fluoro-2-methoxy-benzene and 0.195 g (4.12 mmol) of 1-chloro-3-propanol in 3 ml of dry N,N-dimethyl-formamide were added 92.5 mg (3.09 mmol) of sodium hydride (80% dispersion in refined oil) in 3 portions at one hour intervals. After complete addition the stirring was continued for 2 hours at room temperature, then 2 ml of an saturated aqueous sodium hydrogencarbonate solution were added and the reaction mixture evaporated under reduced pressure. Subsequently, the residue was treated with a mixture of dichloromethane and water, the organic phase was separated and dried over sodium sulfate. Finally, the solvent was evaporated under reduced pressure and the crude product was purified by chromatography on silica gel with a 1:1 mixture of hexane and dichloromethane as the eluent. There were obtained 0.29 g (60% of theory) of 1-(3-chloro-propoxymethyl)-4-fluoro-2-methoxy-benzene as a colorless liquid; MS: 232 (M)+.

Workup

  1. additionAfter complete addition the stirring
  2. customthe reaction mixture evaporated under reduced pressure
  3. additionSubsequently, the residue was treated with a mixture of dichloromethane and water
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. customFinally, the solvent was evaporated under reduced pressure
  7. customthe crude product was purified by chromatography on silica gel with a 1:1 mixture of hexane and dichloromethane as the eluent

Sources & evidence

ORD record
ord-fa38a7a6e3e441228724147adf0777f5
Source dataset
uspto-grants-2002_04
Patent number
US06376672B1

Reaction notes

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