4-Hydroxybenzaldehyde → HCID 12419541, compound

HRID 417751Notes

Reaction equation

HRID 417751 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[CH2:17][CH2:18][CH2:19][C:20]#[N:21]>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:17][CH2:18][CH2:19][C:20]#[N:21])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 214124-Bromobutyronitrile

Product 1

HCID 12419541HCID 12419541, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

Under argon, 2.44 g (20 mmol; 1 eq.) of 4-hydroxybenzaldehyde are dissolved in 20 mL DMF, and 5.53 g (40 mmol; 2 eq.) of K2CO3 are added. After 1 hour's stirring at 70° C., the medium becomes pink. Using a dropping funnel, a solution of 2.4 mL (24 mmol; 1.2 eq.) of 4-bromobutyronitrile in 6 mL DMF are added slowly. The reaction medium is stirred 1 hour at 70° C. then 2 hours at 90° C. After cooling, the medium is filtered through a sintered glass filter. The filtrate is diluted with dichloromethane until precipitation, then filtered again through a sintered glass filter. The new filtrate is concentrated to dryness then re-dissolved in dichloromethane. The organic phase is washed twice in water then with a saturated NaCl solution, dried over Na2SO4 and concentrated to dryness. 4.15 g of compound (11) are obtained and used without any additional purification (quantitative yield).

Workup

  1. stirringThe reaction medium is stirred 1 hour at 70° C.
  2. custom2 hours
  3. customat 90° C
  4. temperatureAfter cooling
  5. filtrationthe medium is filtered through a sintered glass
  6. filtrationfilter
  7. additionThe filtrate is diluted with dichloromethane until precipitation
  8. filtrationfiltered again through a sintered glass
  9. filtrationfilter
  10. concentrationThe new filtrate is concentrated to dryness
  11. dissolutionthen re-dissolved in dichloromethane
  12. washThe organic phase is washed twice in water
  13. dry with materialwith a saturated NaCl solution, dried over Na2SO4
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dee0afe7c73b492aa11d3e4d0d14c468
Source dataset
uspto-grants-2012_01
Patent number
US08092661B2

Reaction notes

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