3-Hydroxybenzaldehyde → HCID 17620948, compound

HRID 550963Notes

Reaction equation

HRID 550963 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH2:19][OH:20].O>CN(C=O)C>[OH:20][CH2:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 17620948HCID 17620948, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxybenzaldehyde (366 mg, 3 mmol) in anhydrous DMF (7 ml), under nitrogen atmosphere, K2CO3 (829 mg, 6 mmol), and, after 10 minutes, 3-bromo-1-propanol (500 mg, 3.6 mmol) were added. The mixture was heated to reflux for 2 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 on Na2SO4. After evaporation of the solvent the crude product was purified by chromatography on silica gel (Petroleum ether/Ethyl acetate 2/1); 520 mg (yield 95%) of title product were obtained.

Workup

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

Sources & evidence

ORD record
ord-218ef2459ce04d8f9e561f2b7ce6754a
Source dataset
uspto-grants-2011_05
Patent number
US07947674B2

Reaction notes

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