4-Hydroxybenzaldehyde → 4-(2-Methoxyethoxy)benzaldehyde

HRID 1595371Notes

Reaction equation

HRID 1595371 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:10][O:11][CH2:12][CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 64855604-(2-Methoxyethoxy)benzaldehydeYield 47.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Hydroxybenzaldehyde (300 g) and 2-chloroethyl methyl ether (279 g) were dissolved in DMF (3 L) and potassium carbonate (408 g) was added. The mixture was stirred with heating at 60° C. for 16 hr. After the reaction, the reaction mixture was poured into water and liberated oil was extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. After drying, the residue was concentrated under reduced pressure to give 4-(2-methoxyethoxy)benzaldehyde as an oil (212 g).

Workup

  1. customAfter the reaction
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with 1N aqueous sodium hydroxide solution
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customAfter drying
  7. concentrationthe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d6a7c5e238a047bc968413ed9a66a171
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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