3-Hydroxybenzaldehyde → HCID 10773659, compound

HRID 639727Notes

Reaction equation

HRID 639727 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:14]=[C:12]([CH3:13])[CH2:11][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 11715Bromoacetone

Product 1

HCID 10773659HCID 10773659, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3.05 g of 3-hydroxybenzaldehyde, 2.3 ml of bromoacetone and 30 ml of dimethylformamide was added 4.15 g of potassium carbonate, and this was heated and stirred at 70° C. for 30 minutes. After cooled to room temperature, insolubles were filtered and the filtrate was concentrated under reduced pressure. Water was added to the resulting residue, and then extracted with ethyl acetate. The organic layer washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to obtain 0.76 g of oily 3-(2-oxo-propoxy)benzaldehyde [Compound No. (o)].

Workup

  1. temperaturethis was heated
  2. temperatureAfter cooled to room temperature
  3. filtrationinsolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the resulting residue
  6. extractionextracted with ethyl acetate
  7. washThe organic layer washed successively with water
  8. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-423a7ab406f041409078e93f13396c8e
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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