Hydrochloric Acid → 3-(3-Chloropropoxy)-4-ethoxybenzaldehyde

HRID 1985830Notes

Reaction equation

HRID 1985830 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][Cl:23].Cl>CN(C)C=O>[Cl:23][CH2:22][CH2:21][CH2:20][O:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[O:3][CH2:1][CH3:2])[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 756794-Ethoxy-3-hydroxybenzaldehyde

Product 1

HCID 231438703-(3-Chloropropoxy)-4-ethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Ethoxy-3-hydroxybenzaldehyde (74.3 g) and potassium carbonate (111.3 g) were suspended in N,N-dimethylformamide (350 mL). To the mixture was added dropwise 1-bromo-3-chloropropane (79.6 mL) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added dropwise 2 mol/L hydrochloric acid (300 mL), and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (69.8 g).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-0a16307589d44ffe931f001e4fffbd83
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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