4-Hydroxybenzaldehyde → Benzaldehyde, 4-(2-hydroxyethoxy)-

HRID 2066084Notes

Reaction equation

HRID 2066084 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([OH:19])[CH3:18].O>CN(C=O)C>[OH:19][CH2:17][CH2:18][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 14202443Ethanol, 1-bromo-

Product 1

HCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-Yield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxybenzaldehyde (366 mg, 3 mmol) in anhydrous DMF (7 ml), under nitrogen atmosphere, K2CO3 (829 mg, 6 mmol), and, after 10 minutes, bromoethanol (450 mg, 3.6 mmol) were added. The mixture was heated to reflux for 3 hours, then water was added and the product was extracted with CH2Cl2. The organic layers were washed with water and with NaCl saturated solution, dried with Na2SO4. After evaporation of the solvent, the crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 2/1); 400 mg (yield 80%) of pure product of the title were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionthe product was extracted with CH2Cl2
  4. washThe organic layers were washed with water and with NaCl saturated solution
  5. dry with materialdried with Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 2/1)

Sources & evidence

ORD record
ord-13a82dcf1d5247d58a51f768766e578a
Source dataset
uspto-grants-2012_10
Patent number
US08288528B2

Reaction notes

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